Photograph by Shawn Owen
From waterfront concerts and outdoor markets to live theater, local festivals, and unique summer experiences, there's no shortage of ways to make the most of the week ahead. Whether you're browsing handmade goods, cheering on the Annapolis Blues, enjoying live music under the stars, or exploring history brought to life, this lineup is packed with opportunities to get outside, support local, and soak up everything summer has to offer.
Wine Down Wednesday
July 8th; The Resin Room, Annapolis 6:00pm
Unwind after a long day with Wine Down Wednesday, a creative evening that pairs art with a little relaxation. Guided by local artist Kylie, participants will create their own beautiful glass art piece while enjoying wine, snacks, and a laid-back atmosphere. Whether you're planning a girls' night, date night, or simply looking to try something new, this hands-on workshop offers the perfect mix of creativity, conversation, and fun. No artistic experience is needed—just bring your imagination and enjoy a sparkling midweek escape.
Dinner Under the Stars
July 8th; First Block of West Street, Annapolis 5:00pm
Enjoy a summer evening in downtown Annapolis during Dinner Under the Stars, where West Street transforms into a lively outdoor dining destination filled with music, great food, and community spirit. This week's performance by Local Souls provides the perfect soundtrack as guests dine al fresco, stroll the closed street, and soak up the festive atmosphere. Whether you're meeting friends for dinner or making it a date night, it's a wonderful way to enjoy live music and support local restaurants. Bring your appetite, your dancing shoes, and celebrate summer under the stars.
7/9 Tides & Tunes: One Night Only
July 9th; Annapolis Maritime Museum, Annapolis 7:00pm
Enjoy a summer evening by the water at this free outdoor concert featuring One Night Only. Bring a chair or blanket, settle in along the waterfront, and take in an evening of live music in a relaxed community setting. Food trucks and beverages will be available for purchase, making it easy to grab dinner while enjoying the performance. It's the perfect opportunity to unwind with family and friends, soak in the waterfront views, and make the most of a warm summer night.
The Talent Machine Presents Curtains: A Musical Comedy Whodunit
July 10th; Anne Arundel Community College, Arnold 7:00pm
Follow the twists, turns, and toe-tapping tunes of Curtains, a Broadway-style musical comedy whodunit presented by The Talent Machine. Featuring a talented cast of local teen performers, this lively production combines murder mystery, laugh-out-loud comedy, and energetic musical numbers into an unforgettable theatrical experience. Set in 1959 Boston, the story follows a theater-loving detective determined to solve a backstage murder before the curtain falls for good. Performances run July 10–12 and July 16–19, making it easy to catch this entertaining summer production.
La Dolce Vita summer pop-up shop is HERE.
July 11th; HERE. A Pop-Up Shop, Annapolis
Discover the best of local shopping during the La Dolce Vita Summer Pop-Up at HERE. a pop-up shop, running daily from July 10 through August 2. Browse handcrafted goods, art, jewelry, home décor, and unique finds from more than 60 local makers while supporting small businesses from across the region. Throughout the pop-up, visitors can also enjoy special events, workshops, and themed shopping experiences, making every visit a little different. Whether you're searching for the perfect gift or simply looking to treat yourself, this month-long celebration of local creativity is well worth a stop.
Revolutionary London Town: Living History Weekend
July 11th -12th; Historic London Town & Gardens, Edgewater 10:00am
Step into the year 1776 during Revolutionary London Town: Living History Weekend, a family-friendly celebration of America's 250th anniversary. Costumed interpreters, colonial militia demonstrations, period music, hands-on crafts, games, and historical reenactments bring the Revolutionary era to life while exploring what independence meant to the people of Maryland. With interactive experiences for all ages and plenty to see throughout the historic grounds, this immersive event offers a fun and memorable way to experience history firsthand.
PlayAnnapolis 3rd Annual Tailgate
July 11th; Navy marine Corps Stadium, Annapolis 5:30pm
Kick off game day while supporting a great cause at PlayAnnapolis' 3rd Annual Tailgate Fundraiser. Enjoy a family-friendly pregame celebration featuring Smokehouse BBQ, music, and a fun community atmosphere before heading into the Annapolis Blues match. Every ticket helps expand access to youth sports for children in Annapolis, making this a great opportunity to cheer on the hometown team while giving back. It's the perfect way to start an evening of soccer, food, and community spirit.
Bastille Day at Sweet Hearts Patisserie & Clock Tower Place
July 11th – 12th; Sweet Hearts Patisserie, Annapolis 8:00am
Say bonjour to a weekend of French-inspired food, wine, and fun during this Bastille Day celebration at Clock Tower Place. Stroll between local businesses offering French pastries, cheeses, wines, specialty menus, and complimentary tastings while enjoying festive activities like grape stomping and fresh crêpes. Whether you're a devoted Francophile or simply looking for a unique culinary experience, this charming celebration offers a delicious taste of France right in the heart of Annapolis.
4th Annual Toss for a Cause Cornhole Tournament
July 11th; Severna Park Elks Lodge, Severna Park 11:00am
Support an important cause while enjoying a day of friendly competition at the 4th Annual Toss for a Cause Cornhole Tournament. This family-friendly fundraiser features cornhole, raffles, great food, and plenty of fun, all while raising money for lung cancer research in memory of Alan Eng. Whether you're competing for the title or cheering from the sidelines, every participant helps make a meaningful impact in the fight against lung cancer. Gather your friends, test your aim, and toss for a great cause.
The Donkey Partnership Experience: Where Kindness Leads the Way
July 11th; Campbell’s Lane Farm, Easton 10:00am
Slow down and discover the power of connection during The Donkey Partnership Experience, a one-of-a-kind workshop designed to foster mindfulness, communication, and confidence through interactions with donkeys. Participants will spend time with the herd before partnering with one donkey for a series of gentle, guided activities that emphasize patience, trust, and kindness. No previous experience is necessary, making this intimate small-group experience a meaningful opportunity to reconnect with yourself while spending time with these remarkable animals.
Naptown Flea
July 12th; Maryland Avenue, Annapolis 10:00am
Spend the day discovering local treasures at Naptown Flea, as Maryland Avenue transforms into a lively marketplace celebrating vintage finds, handmade goods, and small businesses. Browse more than 60 vendors, enjoy live music, grab a drink in the beer garden, and check out unique experiences like flash tattoos while exploring one of Annapolis's most vibrant streets. Whether you're hunting for one-of-a-kind pieces or simply soaking up the atmosphere, this popular community event offers something for everyone.
Maryland Hall Presents BloomHaven
July 12th; Maryland Hall for the Creative Arts, Annapolis 6:00pm
Kick off Maryland Hall's BloomHaven summer concert series with Road to Baygrass: Grateful Dead Night featuring Better Off Dead. Set on the front lawn, this outdoor concert invites fans to enjoy an evening of classic Grateful Dead favorites, extended jams, singalongs, and plenty of dancing beneath the summer sky. Bring a blanket or lawn chair, gather with friends, and experience a laid-back night of live music, community, and unforgettable summer vibes.
Birdies for the Bay
July 12th; Queenstown Harbor Golf Resort, Queenstown 8:30am
Hit the links for a great cause during Birdies for the Bay, a charity golf tournament benefiting the Chesapeake Bay Environmental Center and Coastal Conservation Association Maryland. Enjoy a day of friendly competition while helping support environmental education, habitat restoration, and conservation efforts that protect the Chesapeake Bay for future generations. Whether you're playing for the score or simply soaking in the scenic surroundings, this tournament offers a rewarding way to spend the day while giving back to one of the region's most treasured natural resources.
Tunesday By Chronic Sailing
July 14th; Back Creek Eastport, Annapolis 6:00pm
Enjoy a summer evening on the water during Tunesday, the unique floating concert series that brings live music to the scenic shores of Back Creek. This week's featured performer, Joey Harkum, delivers his signature blend of folk, rock, and soulful songwriting, creating the perfect soundtrack for a sunset on the Chesapeake. Whether you're watching from shore or arriving by boat, this one-of-a-kind community gathering offers a relaxed atmosphere, beautiful waterfront views, and an unforgettable night of live local music.
