Summer Dining Guide 2024

By James Houck and Megan Kotelchuck | Photography by Stephen Buchanan and Tony Lewis, Jr.

The Top Sailor Hangouts, Crab Houses, Waterfront Views, Beach Bars, Raw Bars, Happy Hours, Live Music, Beer Gardens, Taprooms & Oh-So-Much More 

Welcome to our brand-new summer dining guide and completely revised format! This season, we’ve blown the doors off the old restaurant guide and given the keys to our editors, readers, and local restauranteurs to drive the recommendations. 

When you think of summer dining, what comes to mind? Where to pick crabs is near the top of the list. We’ve got our Favorite Crab Houses. Where do boaters like to hang after a day on the water? We’ve offer restaurants with a maritime attitude. Beach bars where you can get sand between the toes? It’s in here. And many more restaurants that epitomize summer relaxation, good eats, the water…the Chesapeake Bay experience! 

To be included in this year’s guide, a restaurant had to tickle the fancy of the editors, be recommended by our readers, be legendary, be surprising, be summery, or be in the What’s Up? Media family of clients. Restaurants are listed alphabetically—not by rank—under each category. 

Don’t see your favorite? Let us know the restaurants you think we missed and who should be considered for next year’s guide. Write to us at: editor@whatsupmag.com. 

** = advertiser within the July issues of What’s Up? Annapolis, What’s Up? Eastern Shore & What’s Up? Central Maryland

Let’s dive into great summer dining!

Top Sailor/Boater/Angler Hangouts

** Boatyard Bar & Grill – 400 Fourth Street, Annapolis; 410-216-6206; boatyardbarandgrill.com; When the patron saint of sailing himself, Jimmy Buffet, frequented an establishment, you know it checks out! Nautical vibe…check! Trophy fish adorning the walls. Yep! Fresh, local seafood and “All killer, no filler” crabcakes—hey, it’s a slogan. Supports local conservation and angling charities—often and annually. And a darn good margarita to wash down the eats while kicking back with like-minded water warriors. It’s the Boatyard! We’re thinking owner Dick Franyo is nearing saint status as well! Read an interview with him here.

Carpenter Street Saloon – 113 S. Talbot Street, St. Michaels; 410-745-5111; carpenterstreetsaloon.com; It’s the heartbeat of St. Michaels. For more than 50 years, the Saloon has served locals and visitors breakfast, lunch, dinner, and plenty of cold drinks to wash it all down. The saloon even runs its own shuttle bus on weekends to help patrons return home or port safely. Live music is also a big draw and keeps the crowds returning season after season.  

Capsize OXMD – 314 Tilghman Street, Oxford; 410-226-5900; capsizeoxmd.com; Come by boat (or land) to this relaxing seafood restaurant overlooking Town Creek in maritime-rich Oxford. This seasonal destination has free dockage while you dine and overnight space if you’re in the mood to stay a little longer. The menu leans on blue crab, lobster, scallops, shrimp, conch…you name it. And the indulgent cocktails cover all bases.  

Davis’ Pub – 400 Chester Avenue, Annapolis; 410-268-7432; davispub.com; Located in the heart of Eastport’s “marina district,” Davis’ is several things: a locals’ hangout, a blue-collar catchall, a quick biz’ lunch spot, a post-boating watering hole, and in recent years, tourist attraction. When famous chef Guy Fieri featured the eatery on his “Diners, Drive-Ins and Dives” television show, Davis’ instantly became a must-visit for out-of-towners seeking uniquely Annapolitan pub-grub. 

Fish Whistle – 100 George Street, Georgetown; 410-275-1603; fishandwhistle.com; A northern Bay destination among boaters, Fish Whistle serves classic Shore seafood, plenty of surprises, and respite right on the beautiful Sassafras River. Located at Granary Marina, there’s plenty of transient or long-term seasonal docking and all the amenities. 

Pusser’s Caribbean Grille – 80 Compromise Street, Annapolis; 410-626-0004; pussersannapolis.com; Sadly, this will be the last summer to enjoy Pusser’s, which has been one of the most attractive dockside bars and restaurants in the heart of Downtown Annapolis for several decades. The new tenant of the space—Atlas Restaurant Group (owners of The Choptank, just a block away)—will transform Pusser’s into two concepts by summer ’25: an upscale Italian chophouse (named Marmo) and a tequila cantina (named Armada). So, enjoy a famed Pusser’s Painkiller before this party ends and another begins.    

Red Eye’s Dock Bar – 428 Kent Narrow Way N., Grasonville; 410-304-2072; redeyesdb.com; Red Eye’s is more than lunch or dinner. It’s more than great waterfront views in Kent Narrows, or even a boaters’ destination. It’s an experience. The Red Eye’s experience. The dock bar and restaurant has become legendary among summer faithful for its stellar live music scene, bikini contests, cold drinks, and filling food. It’s always a party at Red Eye’s!

Favorite Crab Houses

Buddy’s Crabs & Ribs – 100 Main Street, Annapolis; 410-626-1100; buddysonline.com; With million-dollar views overlooking Annapolis’ Market Space and the Ego Alley harbor, Buddy’s is hard to beat for cracking crabs and enjoying a cold bucketful of brews. It’s all-you-can-eat buffet also is renowned. The downtown dining staple is popular with out-of-town visitors, so arrive early to secure a table or spot on the waitlist. 

** Crafty Crab Seafood – 6800 Race Track Road, Bowie; 240-245-3715; craftycrabrestaurant.com; New to the region’s seafood scene is Crafty Crab and its urban “sports bar-meets-picking party” vibe with a decidedly New Orleans influence. The steamed platters are the star here, with your choice of crabs (Blue, Dungeness, Alaskan King, Snow, etc.), other steamer staples (mussels, clams, shrimp, crawdads, lobster), and type of seasoning. The menu is unique, the atmosphere active, and the food delicious! Read our full dining review, here.

Fat Boys Crab House – 1651 MD-3, Crofton; 443-292-4709; fatboyscrofton.com; It’s a western Anne Arundel gathering spot for friends to pick crabs over a few cold ones while watching the game-du-jour on the flat screens above the bar. Indoors and air-conditioning make for comfy confines in which to crack jumbos!

Fisherman’s Crab Deck – 3032 Kent Narrow Way S., Grasonville; 410-827-6666; crabdeck.com; The expansive open-air seating and outdoor deck sits right on the Narrows of Prospect Bay, offering exciting views of the bustling boats, marinas, and Kent Island way of life. The Schulz family has operated the Crab Deck and adjacent Fishermen’s Inn for decades—the entire operation became, and continues to be, a landmark seafood establishment serving jumbo crabs and piles of steamed seafood to patrons who arrive by both boat (ample docking) or car.  Read about the Schulz family legacy here.

Harris Crab House – 433 Kent Narrow Way N., Grasonville; 410-449-5756; harriscrabhouse.com; For more than 75 years, patrons have enjoyed picking crabs freshly harvested, delivered, and steamed on site. Harris is an iconic crab house located on the northern side of the Narrows, surrounded by marina docking, the busy water passage, and maritime culture that defines Kent Island.  

Jimmy Cantler’s Riverside Inn – 458 Forest Beach Road, Annapolis; 410-757-1311; cantlers.com; Waterman-turned-restauranteur Jimmy Cantler and his wife Linda founded what became a destination for crab picking and fresh seafood way back in 1974. Celebrating 50 years, Cantler’s continues to delight guests from near and afar who flock to the tucked-away restaurant that overlooks quiet Mill Creek.  

Mike’s Restaurant & Crab House – 3030 Riva Road, Riva; 410-956-2784; mikescrabhouse.com; Since ’58, Mike’s has served locals and visitors fresh, local seafood in a dock setting overlooking the South River at the Riva Road Bridge. The picnic tables for crab picking are many, boat docking is free and plentiful, and the market-priced blue crabs some of the best on the Bay! Bonus: the Mike’s operating-family purchased the old Sunset Restaurant in Pasadena and transformed into brethren restaurant, Mike’s North.   

Ocean Odyssey – 316 Sunburst Highway, Cambridge; 410-228-8633; toddseafood.com; When a restaurant has a specially-designated “Pickin’ Room,” they must be all about them crabs! And they are—the Todd family business dates back to the 1940s as local seafood processors before jumping into the restaurant venture in the ’80s. Over time, Ocean Odyssey has become synonymous with Cambridge seafood culture. 

The Crab Claw – 304 Burns Street, St. Michaels; 410-745-2900; thecrabclaw.com; What began as a clam and oyster shucking house in the ’50s was turned in a full-service restaurant and crab house by Bill and Sylvia Jones in the ’60s. The Crab Claw, which overlooks the Miles River, remained a summer institution ever since and today, though owned by the adjacent Chesapeake Bay Maritime Museum, remains operated by the same family. 

The Point Crab House & Grill – 700 Mill Creek Road, Arnold; 410-544-5448; thepointcrabhouse.com; If the restaurant was any closer to the water, you’d need a bathing suit to enjoy your meal. Opened by chef Bobby Jones and wife Julie on Mill Creek, just off the Magothy River, The Point has a coastal-casual vibe with upscale taste with a refined dinner menu, and offers classic crab cracking on the outdoor patio or screened-in dining room. 

Waterman’s Crab House – 21055 West Sharp Street, Rock Hall; 410-639-6860; watermanscrabhouse.com; Smack dab in the middle of Rock Hall Harbor sits Waterman’s. With the Chesapeake Bay just beyond nearby jetties, the setting for a complete crab feast with all the fixin’s, delicious crushes, and sunset views is near perfect. 

Top Waterfront Views

Broken Oar Bar & Grille – 864 Nabbs Creek Road, Glen Burnie; 443-818-9070; brokenoarbarandgrill.com; Great food, a rockin’ sushi bar, and panoramic waterfront views of Nabbs Creek…welcome to Glen Burnie! Arrive by boat and get ready for some oarsome food, oarsome beer, and oarsome fun!

** Carrol’s Creek – 410 Severn Avenue, Annapolis; 410-263-8102; carrolscreek.com; Did you know Annapolis’ bustling Spa Creek was once named “Carol’s Creek”? A map discovered in France and brought to Annapolis in 1976 showed that the waterway was originally named after Charles Carroll of Carrollton, our most locally famous signer of the Declaration of Independence. Today, Carrol’s Creek restaurant takes pride in its name by offering an elite menu of fresh and delicious seafood and steaks with amazing views of the creek, marinas, and maritime activity. Read our interview with owner Jeff Jacobs here.

Doc’s Sunset Grille – 104 W Pier Street, Oxford; 410-226-5550; facebook.com/docssunsetgrille; Looking for a spot in Oxford with the perfect view of the Tred Avon River? I’m saving a barstool for you at Doc’s Sunset Grille. Grab a steam pot of your choice, a great crush, and amazing views!

Dock House Restaurant – 110 Piney Narrows Road, Chester; 443-446-4477; dockhouserestaurant.com; The wrap-around deck gives Dock House the perfect panoramic views of the Kent Narrows. You choose whether you are docking your boat at their slips or parking your car in their lot; either way, you’ll enjoy delicious food and crafty cocktails.

Harrison’s Harbour Lights – 101 N Harbor Road, St. Michaels; 410-745-9001; harrisonsharbourlights.com; In 2019, Harrison’s Harbour Lights Restaurant set out on a goal to create the best waterfront restaurant in the state. How do you think they are doing? Harrison’s offers a pear and pecan salad, bacon wrapped scallops, crab imperial stuffed mushrooms, and so many more fresh selections, all with a Miles River view.

Latitude 38 – 12 Dock Street, Annapolis; 667-204-2282; latitude38waterfront.com; Historic Annapolis is full of gems, and not all of them seem to be hidden. Right on the water in downtown Annapolis, overlooking Ego Alley, is your seafood destination—Latitude 38. Latitude 38 even has a banquet room to host you and up to 300 of your closest friends!

** Libbey’s Coastal Kitchen + Cocktails – 357 Pier One Road, Stevensville; 410-604-0999; libbeyscoastalkitchen.com; Along the Eastern Shore, tradition is paramount, and so is family. You may be familiar with the building on the Chesapeake Bay, but meet the family that now owns it. Walt Petrie combined his wife and daughters’ names (Lisa, Lindsay, and Abbey) to create Libbey’s, where the views are stellar and the fresh, local cuisine is even better! Read our interview with the executive chef here.

Marker Five - 6178 Tilghman Island Road, Tilghman; 410-886-1122; markerfive.com; There is something special right between the Eastern Chesapeake Bay and the Choptank River on Knapp’s Narrow: Marker Five. This hidden gem offers a scratch kitchen with fresh ingredients. In addition to delicious seafood, Marker Five offers house-smoked meats, making for the perfect tacos, ribs, pizza toppings, and more.

Rosa Mexicano – 153 Waterfront Street, National Harbor; 301-567-1005; rosamexicano.com; Ready for a fiesta? Elevate the experience at Rosa Mexicano. Rosa Mexicano is a destination born of a unique vision to combine the rich heritage, culinary techniques, and global impact of Mexican cuisine, all while overlooking the National Harbor on the Potomac River.

Severn Inn – 1993 Baltimore Annapolis Boulevard, Annapolis; 410-349-4000; severninn.com; There is no view quite like what you will get from the eastern side of the Naval Academy Bridge at the Severn Inn. Sit on the patio or inside with floor to ceiling windows to truly enjoy a dinner and view of the Academy and Annapolis Harbor.

The Choptank – 110 Compromise Street, Annapolis; 443-808-1992; thechoptankrestaurant.com; Local seafood takes the spotlight on The Choptank’s menu. The Choptank is a modern take of a fish and crab house, serving Maryland’s famous bay cuisine, cocktails, crushes, oysters, and craft beer. Since Summer 2022, Choptank in has been an indoor/outdoor dining destination overlooking Annapolis’ Ego Alley and Market Space.

Yellowfin – 2840 Solomons Island Road, Edgewater; 410-573-1333; yellowfinedgewater.com; There is plenty to look forward to at Yellowfin. Whether it’s fresh fish, crabcakes, steak, scallops, or sushi, there are more than enough reasons to dine on the South River, especially when you time your visit with an amazing sunset view!

Favorite Beer Gardens / Taprooms

Chessie’s Wharf – 609 Melvin Avenue, Annapolis; 443-603-12135; rarbrewing.com; From RaR Brewing with love, comes Chessie’s Wharf, a new taproom in West Annapolis with a beer hall atmosphere where you’ll make new friends over cold pints. We especially enjoy the wall of “Big Mouth Billy Bass” that sings on the hour!  

Crooked Crab – 8251 Telegraph Road, Ste. D, Odenton; 443-569-9187; crookedcrabbrewing.com; With large vats of actively brewing beer visible from the taproom, what you see is what you’re getting! Serving a 36-tap rotation of seasonals and classic style beers (including mead!), Crooked Crab also offers brick oven pizzas to help tame the buzz. And the outdoor seating in the parking lot has that pop-up vibe that feels like a Sunday afternoon tailgate. 

Cult Classic Brewing – 1169 Shopping Center Road, Stevensville; 410-980-8097; cultclassicbrewing.com; Since opening in summer 2018, Cult Classic has become a Kent Island destination—a place to enjoy fresh, local brews in an expansive taproom that also hosts rousing live music, talent and trivia nights, and more. 

Forward Brewing – 418 Fourth Street, Annapolis; 443-221-7277; forwardeastport.com; If sipping fresh, on site-crafted beer with your besties in the rich maritime Eastport community sounds like a fun idea, look no further than Forward Brewing.   

Garten – 849 Baltimore Annapolis Boulevard, Severna Park; 443-261-3905; garten-eats.com; The Old World never felt so new and exciting. Garten is the brainchild of Jeremy and Michelle Hoffman, owners of Preserve in Annapolis. The farm-to-table concept is refined with German and French influence, and both indoor and outdoor dining areas in which to toast fine food with good friends.  

Heroes Pub – 1 Riverview Avenue, Annapolis; 410-573-1996; heroespub.com; A pub that pays homage to first responders, Heroes was, perhaps, the first of its kind in Annapolis—a bar with more than 40 taps lined up and primed to deliver quality craft beer. Play darts over a couple pints, order the best wings in town, and enjoy Annapolitan camaraderie.  

Lures Bar & Grille – 1397 Generals Highway, Crownsville; 410-923-1606; luresbarandgrille.com; The woodsy vibe of the outdoor beer garden lends well to shady summer and fall days spent enjoying a few beer selections from Lures’ expertly-curated menu, along with fresh nibbles (rockfish bites!) and chef selections that lean on daily market fish and seafood. 

** Old Stein Inn – 1143 Central Avenue, Edgewater; 410-798-6807; oldstein-inn.com; Authentically German from stein to schnitzel, this south county gem has been a destination since the 1980s when Karl & Ursula Selinger emigrated from Rhineland Pfalz to open the restaurant (now run by son Mike). Today, Old Stein’s outdoor biergarten is a four-season experience not to be missed. Read our latest interview with owner Mike Selinger here.

Pherm Brewing Company – 1041 MD-3, Gambrills; 443-302-2535; phermbrewing.com; It seems the west Anne Arundel County community can’t get enough of Pherm’s heady brews. The young company has already expanded its footprint, doubling in size to craft delicious concoctions. The taproom features live music, open mics, trivia nights, and, sometimes, yoga sessions. Bottoms up!

RaR Taproom – 504 Poplar Street, Cambridge; 443-225-5664; rarbrewing.com; The flagship taproom of RaR Brewing is located in Cambridge. It’s an original, from the onsite brewing to cedar top bar and local artwork—a place where gathering with friends to share a pint is a uniquely rewarding experience. 

Jailbreak Brewing Company – 9445 Washington Boulevard N., Ste. F, Laurel; 443-345-9699; jailbreakbrewing.com; HoCo’s first production brewery, Jailbreak gained a following in Laurel and the surrounding communities for its precision crafted brews and approach to accompanying eats. The “Foodworks” side of the taproom offers a hearty menu of handhelds, flatbreads, and dry-aged meats.

Top Beach / Tiki Vibes

Big Owl Tiki Bar – 3015 Kent Narrows Way S., Grasonville; 410-827-6523; thebigowl.com; From live music to Sunset DJ Parties, Big Owl Tiki Bar is a glorious beach bar right on the Kent Narrows just waiting for you to bring the party! 

Coconut Joe’s Bar & Grill – 48 South River Road, Edgewater; 443-837-6057; coconutjoesmd.com; Feel like you are at the beach with indoor/outdoor dining, three bars, including two tikis overlooking the South River. Make the day even better by enjoying the large sand-filled play area with a brand-new pirate ship for the kiddos.

Foxy’s Harbor Grille – 125 Mulberry Street, St. Michaels; 410-745-4340; foxysharborgrille.com; Ready to visit paradise without a passport? Foxy’s offers Caribbean-style dishes, Maryland crabcakes, local seafood, and more right in the St. Michaels Marina.

Harbor Shack – 20895 Bayside Avenue, Rock Hall; 410-639-9996; harborshack.net; In 2006, the plan was to create Rock Hall’s go-to place for drinking, dining, and entertainment; it is safe to say this neighborhood hangout has succeeded. The Harbor Shack has one of the best views of the Rock Hall Harbor with an eclectic, fun, and upbeat atmosphere on the Upper Eastern Shore.

The Jetty Restaurant & Dock – 201 Wells Cove Road, Grasonville; 410-827-4959; jettydockbar.com; The Jetty has a packed social calendar, with live music all the time, but there is also a chance for you to get involved. Enjoy trivia night, karaoke, bingo, and so much more on the Kent Narrows.

Lowes Wharf Bayside Grill & Tiki Bar – 21651 Lowes Wharf Road, Sherwood; 410-745-6684; loweswharf.com; Ice cold beer, cocktails, tasty treats...is there anything else we are missing? Oh yeah! Live weekend music. See ya at Lowes Wharf soon!

Pirate’s Cove Restaurant & Dock Bar – 4817 Riverside Drive, Galesville; 410-867-2300; piratescovemd.com; The Dock Bar at Pirate’s Cove overlooks the West River with weekend entertainment, locally caught seafood specials, and a vast selection of beers, cocktails, and wine. Anyone want to join us for happy hour?

Rams Head Dockside – 1702 Furnace Drive, Glen Burnie; 410-590-2280; ramsheaddockside.com; Rams Heads’ pub grub and delicious entrees are served in a casual roadhouse-meets-beach bar atmosphere that overlooks Furnace Creek, complete with sandy beach, picnic tables, and palm trees!

The Sandbar at Rolphs Wharf Marina – 1008 Rolphs Wharf Road, Chestertown; 410-778-6347; rolphswharfmarina.com; Rolphs Wharf Marina offers more than just a great place to dock the boat on the Chester River. Grab a cocktail and watch the sun set tonight with sand between your toes.

The Shanty Beach Bar at Tolchester Marina – 21085 Tolchester Beach Road, Chestertown; 410-778-1400; tolchestermarina.com; Want me to spill what is considered the best kept secret on the Bay? The Shanty Beach Bar with their live entertainment and mudslides holds the key. 

Snappers Waterfront Cafe – 112 Commerce Street, Cambridge; 410-228-0112; snapperswaterfrontcafe.com; Cambridge Creek looks great from a place where locals and tourists alike can gather and relax: Snappers! Snappers has something for everyone whether you are in the mood for local crabcakes or Jamaican-inspired seafood and chicken dishes. 

Fave Surf & Turf Restaurants

Blackwall Hitch – 400 Sixth Street, Annapolis; 410-263-3454; blackwallhitchannapolis.com; The nautical-meets-farmhouse design is omnipresent at Blackwall Hitch, from the upscale décor to the inspired menu, which features Chesapeake cuisine and locally-sourced meats. 

Chart House Prime – 300 Second Street, Annapolis; 410-268-7166; charthouseprime.com; Long-revered along Eastport’s “Restaurant Row” for its classic ’n classy menu and million-dollar views of Spa Creek, Chart House received million-dollar renovation recently and is primed to continue hosting your special occasion dinners.  

Knoxie’s Table – 180 Pier One Road, Stevensville; 443-249-5777; baybeachclub.com; Comfortable yet refined, Knoxie’s offers a fresh, farm-to-table and catch-of-the-day dining experience that features all the classics (crabcakes, rockfish, rack-of-lamb, New York strip) and plenty of fun, surprising dishes! Read our full dining review here.

** Lewnes’ Steakhouse – 401 Fourth Street, Annapolis; 410-263-1617; lewnessteakhouse.com; An Annapolis institution since 1921, the Lewnes family continues to host an impeccable dining experience, in which cuts of U.S. Prime beef, lamb, chicken, and market fresh seafood are the stars. Look no further than Lewnes’ for a dinner that’s sure to impress. Read our full dining review here.

O’Learys Seafood Restaurant – 310 Third Street, Annapolis; 410-263-0884; olearysseafood.com; In the heart of Annapolis’ Eastport maritime district, O’Learys exemplifies fine dining, leaning heavily on the freshest seafood available for its culinary creations. While all manner of local and flown-in seafood shine here, don’t overlook the Delmonico steak, Berkshire chops, or the craft cocktails. 

Suicide Bridge Restaurant – 6304 Suicide Bridge Road, Hurlock; 410-943-4689; suicide-bridge-restaurant.com; Despite its namesake (which has an interesting history), this restaurant is heavenly and well-known among Shore locals for fresh seafood and steak selections; and their renowned “once-a-month” Friday buffet. 

Top Raw Bars

McGarvey’s Saloon & Oyster Bar – 8 Market Space, Annapolis; 410-263-5700; mcgarveysannapolis.com; For more than 45 years, McGarvey’s has been serving oysters and fresh seafood in the heart of Annapolis. Can’t figure out what you want from the Raw Bar? Not to worry, the Waterman’s Sampler is calling your name.

O’Brien’s Oyster Bar & Seafood Tavern – 113 Main Street, Annapolis; 410-268-6288; obriensoysterbar.com; Not only does O’Brien’s offer an extensive raw bar, but they are also helping give back to our Bay. O’Brien’s is a partner of Oyster Recovery Partnership to help repopulate the oyster environment in the Chesapeake Bay. The shells of every oyster you suck down at O’Brien’s end up back in the Bay.

Ruse – 209 N. Talbot Street, St. Michaels; 410-745-8011; ruserestaurant.com; Ruse offers an oyster bar as an ode to the rich nautical history of the Eastern Shore, allowing them to showcase a variety of oysters and shellfish from the Chesapeake and other American waterways. I wonder what else Chef Michael Correll is cooking up tonight.

Sailor Oyster Bar – 196 West Street, Annapolis; 410-571-5449; sailoroysterbar.com; Looking for the raw bar of your dreams? I think I found the place right here in Annapolis. Local oysters, Japanese Madai Snapper Sashimi, Salmon Crudo, Tuna Tartar toast. Sailor Oyster Bar is open again (completely renovated after a fire); so, take advantage of this unique dining experience!

Skipper’s Pier – 6158 Drum Point Road, Deale; 410-867-7110; skipperspier.com; The oyster bar consists of more than just raw oysters at Skipper’s. Try out the Crab Crusted Oysters, featuring Chesapeake Bay havrvest oysters with blue crab, garlic herb butter, bacon, parmesan, and beurre blanc. Yum! 

Fave Grab ‘n Go / Market Options

** Eat Sprout – Locations in Easton, St. Michaels, and Annapolis; eatsprout.com; Creating wholesome, nutritious, and absolutely delicious offerings (sandwiches, salads, entrees, drinks) for patrons that care about good health and great food is the mission of Eat Sprout. Husband/wife duo Ryan and Emily Groll founded Eat Sprout with scratch-made and organic in mind, and the business hasn’t looked back, opening anew most recently in Annapolis.   

Fishpaws Marketplace – 954 Ritchie Highway, Arnold; 410-647-7363; fishpawsmarket.com; Gourmet grab ’n go options include everything you could possibly put on a charcuterie board, plus wines, mixers, sodas, and growlers/crowlers of fresh, local brews. Perfect for putting together a primo picnic! Read our interview with owner Kim Lawson here.

Giolitti Fine Italian Market – 2068 Somerville Road, Annapolis; 410-266-8600; giolittideli.com; In the heart of Annapolis’ Parole community, Giolitti has served Annapolitans top-notch, homemade Italian fare, deli subs and sandwiches, and to-go meals since 1992. The market goods and fine wines are also worth the trip. 

** Piazza Italian Market – 218 N. Washington Street, Ste. 23, Easton; 410-820-8281; piazzaitalianmarket.com; Boasting a “curated pantry” of Italian food staples and culinary curiosities, Piazza also features a deli case with both popular and rare cheeses, cured meats, paninis (for that grab ’n go lunch), plus a kitchen that whips up prepared meals-to-go (lasagnas, meatballs, etc.). Read our interview with owner Emily Chandler here.

Seasons Olive Oil & Vinegar Taproom – 180 Main Street, Annapolis; 410-280-1505; seasonstaproom.com; Fresh, naturally flavored oils and vinegars will help dress up your dishes at home. You can sample here, then purchase and take home to whip up your culinary creations. 

The Spice & Tea Exchange – 155 Main Street, Annapolis; 410-280-2088; spiceandtea.com; If you’re looking to up your kitchen-game and add unique flavor to your cooking, the spices and blends you’ll find at this artisan retail shop are certain to help. 

The Winery – 116 S. Piney Road, Ste. 104, Chester; 410-643-9466; thewineryki.com; A go-to for Kent Islanders’ every party and picnicking libations and nibbles need. This store has it all, from gourmet meats and cheeses to fine wines, and even cigars. Read our recent interview with owner Jennifer DiDonato here.

Top Happy Hours

Amalfi Coast Italian + Wine Bar – 401 Love Point Road, Stevensville; 443-249-3426; amalficoastki.com; Does $8 apps and $2 off house cocktails and wines by the glass sound like a deal to you? Visit Amalfi Coast Monday through Friday from 3:30 to 6:30 p.m. Want to make the deal even better? Wine bottles are half-priced every Monday and Wednesday.

The Goat – 137 Prince George Street, Annapolis; 410-571-5577; thegoatannapolis.com; New to Annapolis is The Goat, which features happy hour every day from 2 to 5 p.m. Not only does The Goat have a great food menu, but also a delicious craft cocktail menu featuring homemade bloody Marys, local rotating drafts, and Rise Up Coffee.

The Hideaway – 1439 Odenton Road, Odenton; 410-874-7300; hideawayodenton.com; Award-winning wings, smoked ribs, and adobo burnt ends tacos are all on the Hideaway Happy Hour menu in Odenton. Now’s your chance to try the Blackberry Chipotle Wings while sipping a craft pint.

** Hunters’ Tavern – 101 East Dover Street, Easton; 410-822-4034; tidewaterinn.com; Hunters’ Tavern is nestled inside Tidewater Inn with happy hour Sunday through Thursday from 3:30 to 6 p.m. The menu consists of delicious bites like capicola flatbread and nacho cauliflower popcorn with wine, sangria, domestic bottle deals, and more! Read our full dining review here.

Tuscan Prime Italian Chophouse & Dolce Bar – 1905 Towne Centre Boulevard, Annapolis; 443-572-4677; tuscanprime.com; Who says happiness should only last an hour? We, for sure, don’t, and neither does Tuscan Prime. Enjoy a long list of happy hour options Sunday through Thursday from 4 to 7 p.m., Tuesdays from 4 p.m. to close, and all-day Wednesdays. Read our full dining review here.

Favorite Ice Cream Shops

** Always Ice Cream – Locations in Annapolis, Edgewater, Pasadena, Crofton, Severna Park, and more; alwaysicecreamcompany.com; Downtown Annapolis locals and visitors have long enjoyed the flagship scoop shop on Main Street, and as the company’s delectable, creamy creations became increasingly popular, the Cohen family grew the business into neighboring communities—and always gives back, supporting local charities. Read our interview with the Cohens here.

Kilwins – 128 Main Street, Annapolis; 410-263-2601; kilwins.com; There’s amazing ice cream, yes…but Kilwins is much more than that with cases of handmade chocolates, candies, dipped pretzels, cookies, fudge, so on and so forth.

Scottish Highland Creamery – 103 S. Morris Street and 314 Tilghman Street, Oxford; 410-924-6298; scottishhighlandcreamery.com; Using fresh, locally-sourced milk and cream and traditional techniques, the creamery has made each batch of ice cream by hand since its opening in 2005. 

Storm Bros. Ice Cream Factory – 130 Dock Street, Annapolis; 410-263-3376; stormbros.com; Since 1976, this straightforward scoop shop has served strollers along Annapolis’ Ego Alley. No frills, all chills ice cream flavors keep the lines long all summer long. 

Sugar Doodles Sweet Shop – Locations in Chester, Centreville, and Chestertown; sugardoodlessweetshop.com; Serving delicious Vanderwende Farm Creamery’s ice cream, plus every imaginable topping, Sugar Doodles has become a go-to for Kent Islanders and Shore-bound visitors for sweet treats, shakes, and even healthy acai bowls. 

For Marina Cuisine

Beacon Waterfront Galley & Bar – 2020 Chesapeake Harbour Drive E., Annapolis; 443-949-8456; beaconwaterfront.com; Located in the heart of Chesapeake Harbour’s marina and surrounded by the bayfront community of the same name, Beacon is ship-shape to serve cold drinks, nibbles, steamed seafood, crabcakes, hand-helds, and filling entrees. 

Bridges on Kent Narrows – 321 Wells Cove Road, Grasonville; 410-827-0282; bridgesrestaurant.net; Water, water everywhere! The Narrows, Wells Cove, and Prospect Bay surround this peninsula restaurant that boasts indoor and outdoor seating; a robust menu of surf ’n turf selections, sandwiches, pizzas, and sweets; docking; and close proximity to multiple marinas.  

Deep Blue at Kitty Knight – 14028 Augustine Herman Highway, Galena; 410-648-5200; deepbluerestaurant.com; Overlooking the bustling marinas along the Sassafras River, Deep Blue offers both white tablecloth dining and more casual outdoor seating; perfect respite for refined palettes after a day of boating.

Harper’s Waterfront – 1107 Turkey Point Road, Edgewater; 410-798-8338; harperswaterfront.com; Nestled between Selby Bay and Ramsay Lake just off the South River, Harper’s is the go-to for coastal cuisine in this marina-packed spot. Opening in 2023, Harper’s has quickly earned its reputation as a fine dining establishment with a maritime vibe and top tier service. Read our full dining review here.

Osprey Point – 20786 Rock Hall Avenue, Rock Hall; 410-639-2194; ospreypoint.com; Located in Rock Hall’s protected harbor enclave, Osprey Point is near docking port and starboard, and even welcomes transient guests to their own, full-service, all-amenity marinas. The restaurant is white-tablecloth with a seasonal American menu.  

For Live Music

The Boathouse – 604 Cabana Boulevard, Deale; 410-867-9668; theboathousedeale.com; There is plenty happening in Deale this summer. Check out The Boathouse at Anchored Inn for live music and a good time. Their music schedule is updated on Facebook. 

** Corah’s Corner – 105 N. Talbot Street, St. Michaels; 410-745-8008; corahs.com; Grab a table on the porch at Corah’s Corner and get ready for a relaxing night or food, drinks, and live music. Looking for a quick and cheap date night? Have a dessert cocktail on the porch while listening to local performers. Salted Carmel Cocoa with toffee whiskey anyone?

Killarney House – 584 West Central Avenue, Davidsonville; 410-798-8700; killarneyhousepub.com; It’s always a hoot at Killarney House. There is live Irish music every Wednesday through Saturday, weekend brunch, and plenty of other can’t-miss specials; even Ladies Night every Thursday.

** Rams Head On Stage – 33 West Street, Annapolis; 410-268-4545; ramsheadonstage.com; One of the staples of Annapolis is Rams Head On Stage. Since 1989, locals have been loving live music performed at the renowned Rams Head. This is your chance to see national acts in a very intimate venue, at dining tables complete with full service, a delicious menu, and local brews. Take a look at their website to see who is playing next!

The Rumor Reel – 1701 Poplar Ridge Road, Pasadena; 443-702-2188; therumorreelpasadena.com; Get your mahi, meatloaf, and meatballs, plus a huge serving of live music! The “Electric Eel” stage at the Rumor Reel hosts live music Thursdays through Sundays. The full schedule is updated on their website. 

Stan & Joe’s – 37 West Street, Annapolis; 410-263-1993; stanandjoessaloon.com; Stan & Joes is an Annapolis bar-music destination. Be entertained by local musicians daily at their Annapolis (flagship) or Galesville (riverside) locations; during Dinner Under the Stars on West Street (Wednesdays and Saturdays through end of September) and First Sunday Arts (every first Sunday of the month through November), Stan & Joe’s hosts performers in the adjacent parking lot.

Destination Worthy Restaurants

** Agave – 106 Annapolis Street, Annapolis; 410-449-3980; agaverestaurants.com; Serving traditional and modern Mexican cuisine, hand-squeezed margs, and more than 100 fine tequilas to try, Agave blends upscale ethnic dishes and craft drinks within a newly renovated space that has a bright, uplifting, hacienda aesthetic.

** Akira Ramen & Izakaya – 1417 S. Main Chapel Way, Ste. 108, Gambrills; 301-968-2182; waughchapelakiraramen.com; Served in a slick, modern dining room in which the waft of Japanese cuisine temps you to order everything on the menu, the ramen (noodle/broth based dishes) and izakaya (Japanese style pub) experience is worth trying…and repeating. 

Ava’s Pizzeria & Wine Bar – Locations in St. Michaels, Cambridge, and Rehoboth Beach; avaspizzeria.com; Crisp, artisanal, brick-oven fired and deep-dish pizzas are the hallmark here, but other popular dishes include the homemade meatballs and Italian entrees. The wine and cocktail selections offer perfect pairings for every palate. Read our recent interview with owner Chris Agharbi here.

** Bella Italia Annapolis – 609 Taylor Avenue, Annapolis; 410-216-6061; bellaitaliamd.com; Across Rowe Boulevard from the Navy-Marine Corps Memorial Stadium, Bella Italia draws Midshipmen, locals, and all fans of homemade Italian cuisine served in a casual setting. Owner Lino Chiaro brought home cooking from his native Italy direct to Naptown. Read our interview with him here.

** Carpaccio Tuscan Kitchen / Wine Bar – 1 Park Place, Ste. 10, Annapolis; 410-268-6569; carpacciotuscankitchen.com; Located in the uptown “piazza” at Park Place, Carpaccio offers an upscale experience with classic Italian cuisine and an expertly crafted wine list. Lunch and dinner crowds can be a who’s who of townies and on gorgeous afternoons, sipping a Bellini while nibbling charcuterie on the outdoor veranda might have you second-guessing if you’re in the Old World or new.  

** Della Notte – 1374 Cape St. Claire Road, Annapolis; 410-757-2919; dellanotterestaurant.com; New and exciting, Della Notte has quickly gained favor among Cape locals as the go-to restaurant for hearty Italian fare, fine drinks, and welcoming atmosphere. Read our full dining review here.

** Galliano Italian Restaurant & Wine Bar – 2630 Chapel Lake Drive, Gambrills; 410-721-5522; gallianoitalianrestaurant.com; Galliano has elevated the dining scene in Gambrills/Crofton’s Waugh Chapel complex with the white tablecloth, refined Italian cuisine experience. Attention to detail, from front-of-house to the line to each plate served, is a hallmark.

** Harvest Thyme Modern Kitchen & Tavern – 1251 W. Central Avenue, Davidsonville; 443-203-6846; harvestthymetavern.com; Harvest Thyme has all the fixings of a trendy-meets-traditional, farm-to-table dining experience. The menu leans heavily on the craft and skill of the kitchen (open and visible to diners) with fine meats, seafood, and veggies expertly prepared. The wood-fired pizzas are a hit, and you won’t go thirsty from the floor-to-ceiling wine racks/selections ready to pop. Read our full dining review here.

** Jalapenos – 85 Forest Drive, Annapolis; 410-266-7580; jalapenosonline.com; Long revered for authentic Spanish and Mexican-influenced cuisine, Jalapenos offers upscale, full-service dining perfect for a special night out. Read our full dining review here.

Jesse Jays – 5471 Muddy Creek Road, Churchton; 240-903-8100; jessejays.com; The Latin-inspired kitchen of Chef Jesse Ramirez and talent of wife Jayleen have made one of the newer South County restaurant a absolute hit among diners eager for delicious street tacos, slow roasted meats, traditional dishes, and inspired cocktails.  

Julep Southern Kitchen & Bar – 2207 Forest Drive, Unit 2, Annapolis; 410-571-3923; julepannapolis.com; The brainchild of owner/chef/pitmaster Bob Krohn, Julep represents an affinity for southern charm and comfort food in a refined atmosphere—think classic barbecue with, yes, a mint julep in hand. Read our interview with Julep’s pastry chef, Kate Boccanfuso here.

** Lasang Pinoy – 1000 Annapolis Mall, Space 187, Annapolis; 443-949-9580; lasangpinoyllc.com; New, hip, fine, and fusion begin to describe Lasang Pinoy. The eatery offers a Filipino-influenced menu with wide range of exotic flavors and comfort concoctions that nod to traditional dishes and hint at innovative concepts. Read our interview with owners Neil and Quiza Nichols here.

Lime & Salt – 8395 Piney Orchard Parkway, Odenton; 410-874-6277; limeandsalt.co; A taqueria and agave bar (that’s code for choice tacos and tequila), Lime & Salt is so much more than handhelds and rimmed glasses. With a full fleet of authentic dishes and fresh cocktails, the restaurant has garnered local acclaim and a loyal following. Read our full dining review here.

Main & Market – 914 Bay Ridge Road, Annapolis; 410-626-0388; mainandmarket.com; With a Euro-café feel and expertly prepared dishes and delights to match, Main & Market has drawn the Bay Ridge community to the eatery for more than a quarter-century. And chances are you’ve been to an event catered by them—they’ve won Best Caterer honors in the annual Best of Annapolis readers’ poll for many years. Read our full dining review here.

** Mamma Roma – 8743 Piney Orchard Parkway, Odenton; 410-695-0247; mammaromas.com; Mamma Teresa rules the roost (she still takes orders front-of-house), but sons Bruno and Rino Romeo have taken over operations and the kitchen, and made this family-style restaurant one of the most comforting, authentic, and filling in the region. Odenton residents and visitors from afar can’t get enough! Read our latest interview with here.

** Mi Lindo Cancun Grill – 2134 Forest Drive, Annapolis; 410-571-0500; lindocancungrill.com; Mi Lindo represents the dream of owner Fredy Salmoran who came to the U.S. from Mexico at age 17 in 1999. He began working in the restaurant industry and by 2016 opened his own…Mi Lindo. Today, Fredy and his sons own and operate several more Mexican restaurants, including Senor’s Chile locations in Edgewater, Arnold, and Severna Park. Their success is built upon authenticity and consistently excellent food. Read our interview with the Salmoran family here.

Miss Shirley’s Café – 1 Park Place, Annapolis; 410-268-5171; missshirleys.com; Breakfast, brunch, or lunch on your mind? Miss Shirley’s epitomizes all three with a robust menu of creative dishes, which boast southern and Chesapeake influence…to the max! Skillets, chicken ’n waffles, signature omelets and pancakes, and creative sandwiches, salads, and more are all adored! Read our full dining review here.

Osteria 177 – 177 Main Street, Annapolis; 410-267-7700; osteria177.com; Owner/chef Arturo Ottaviano had a dream to bring his native Italian recipes and experience to the states and by 2006 opened Osteria 177 on the most famed street in Annapolis. In short, the restaurant instantly elevated the restaurant scene and remains one of the finest dining experiences downtown. Read our full dining review here.

** The Galley – 305 S. Talbot Street, St. Michaels; 410-200-8572; thegalleysaintmichaels.com; An annual Best of Eastern Shore winner for breakfast and brunch, The Galley is a locals’ favorite and visitors’ discovery, offering a hearty menu of classic a.m. cuisine, lunchtime specials, and delectable drinks. Read our full dining review here.