From crab feasts and classic rock coffeehouses to garden strolls and drag show birthday bashes, this week is stacked with summer fun. Sip Italian wines at La Dolce Vita, bid on fine art from maritime masters, or cool off with live music and local brews. Whether you’re learning to play tennis, cheering on nonprofits at a pickleball showdown, or dancing the night away at a 7th birthday party (with $7 drinks!), there’s something happening every day to keep your summer lively and local.
TVFC Old Tyme Fair
July 31st – August 1st; Trappe Volunteer Fire Company, Easton
The TVFC Old Tyme Fair is back for 2025—now with new dates! Join the Trappe Volunteer Fire Company for three days of hometown fun, happening Thursday, July 31 through Saturday, August 2 at the Fire House grounds. Enjoy delicious food with nightly specials, hayrides, raffles, fire truck rides, games, a silent auction, and fun for the whole family. Don’t miss the beloved Saturday night parade, a local favorite!
Free Family Tennis - Learn to Play!
July 31st, August 2nd; Truxton Park Tennis and Pickleball Courts, Annapolis 4:00pm – 5:30pm
For ages 5 to 17 and parents and adults! Come learn to play tennis with games and instruction. Rackets provided. Registration is on site. This is a free program supported by the Tennis Alliance and the City of Annapolis Recreation and Parks Department.
La Dolce Vita: Sip & Savor the Taste of Italy
July 31st; Dover station, Easton 6:00pm – 9:00pm
Join Laurie Forster, The Wine Coach, at Dover Station to indulge in La Dolce Vita—Italian-style. Join us for a wine tasting featuring Oak Creek Catering that brings the beauty, flavor, and flair of Italy straight to your glass. Paired with an after hours shopping experience at The Market. We’ll explore refreshing whites, vibrant rosés, and bold reds that capture the spirit of Italy from north to south. Think sun-drenched vineyards, leisurely toasts, and the simple joy of savoring la vita bella. Come thirsty—and ready to toast to summer, Italian-style. Tasting includes an hors d'oeuvre reception, 3 pairing courses, wine tastings, dessert, tax, tips and unlimited wine edutainment from The Wine Coach. Tickets are $125 per person, and advance purchase is required.
The Rotary Club of Annapolis Crab Feast
August 1st; Navy Marine Corps Memorial Stadium, Annapolis 5:00pm
This well-known Annapolis event is a major fundraiser for our local community that benefits many different non-profit organizations. This is an all-you-can eat feast, along with other food options, beer, water and soda. We also host a bake sale for all of those with a sweet tooth! Please save the date and be on the lookout soon for ticket sales!
Fine Art Auction Online Only
August 1st- August 15th; Annapolis Maritime Museum, Annapolis
These items are up for auction by Annapolis Marine Art Gallery. Some are original paintings and others signed prints or photographs. They showcase famous marine artists such as Franklin A. Saye, William Stille, Carl G. Evers, David Tutwiler and Willard Bond. 25 Marine Art Pieces available at auction for a fraction of the price! Bidding begins August 1st at 7am and ends August 15th at 7pm.
Guided Garden Stroll
August 1st; William Paca House and Garden, Annapolis 9:30am – 10:15am
Take a stroll through our beautifully restored two-acre 18th century English garden. Painstakingly restored to its original splendor using details drawn from historic artwork and archaeological excavations, the colonial William Paca Garden is a picturesque retreat from the bustle of the city. Your experienced docent will share its history from the time of William Paca, signer of the Declaration of Independence, to present day as you wander the terraced landscape, formal parterres, wilderness garden, the practical kitchen and medicinal gardens, and orchard. The charming Summerhouse beckons visitors to cross the latticework bridge over a fish-shaped pond.
Emma Huckabee Performs Live at Captain's Daughter
August 1st; Captains Daughter, Annapolis 5:00pm – 7:00pm
Enjoy a summer evening of live music with Emma Huckabee at Captain’s Daughter in Annapolis on Friday, August 1, from 5:00 PM to 7:00 PM. Known for her smooth vocals and soulful sound, Emma brings a mix of original songs and familiar favorites to the stage. Grab a drink, settle in, and soak up the good vibes at one of Annapolis’ coziest spots—perfect for starting your weekend off right.
Peace Love Pickleball
August 1st; The Dink/ The Put Away, Annapolis 6:00pm – 9:00pm
Come Cheer on you favorite non-profit at this friendly, indoor Pickleball competition. Anne Arundel County Food Bank, Charting Careers, The Light House Shelter, Hospice of the Chesapeake, Rise and Shine Bakery and STAIR (Start the Adventure in Reading) each have 3 teams competing for the win and the most funds raised! Sponsored by the Hussman Foundation, 100% of proceeds go to your chosen team. Tickets include food, drink, same-day sign up for beginners skills clinic and an evening of fun with your neighbors. Event open with an exhibition game played by some of our local legislators.
SE7ENth B-Day & FREE Concert
August 1st; Cult Classic Brewing Company, Stevensville 7:00pm – 11:00pm
We’re turning SE7EN, and you’re invited to celebrate with us on Friday, August 1 at 7 PM. Enjoy $7 beers, wines, and margaritas, free birthday cake, and a free live concert from MXD—a powerhouse trio covering six decades of music with energy, nostalgia, and edge.
Bring a wrapped gift (new or used) for the brewery—something fun or vintage we can display—and you’ll get a raffle ticket and a drink ticket in return. Bonus points if you come dressed as your favorite deadly sin. Let’s make it a night to remember.
Casey Cares Foundation 5K Run/Walk
August 2nd; Maryland Zoo, Baltimore 8:00am
We greatly appreciate everyone who joined us for our highly anticipated 15th Annual 5K/1-Mile Walk at the Maryland Zoo! Thanks to your registration and participation, you'll be supporting our various palliative programs for thousands of critically ill children.
Birthdays are a DRAG
August 2nd; Cult Classic Brewing Company, Stevensville; 8:00pm – 11:00pm
Help us blow out our candles as we turn 7 and you catch the greatest drag show in in town. The Queens return August 2. Assemble your crew and prepare to make it rain. Reserved seats at tables are $15. General admission (standing) is $10 per person. Get here early, Cult Classic has 15+ beers on tap brewed in house, a full kitchen with from-scratch pizza, hand-pattied burgers and fresh-never-frozen jumbo wings, and a FULL BAR to get you through this most epic of evenings. Doors open at 8:00
Yoga on the Farm
August 3rd; Maryland Therapeutic Riding, Annapolis 9:00am – 10:00am
Embrace tranquility surrounded by our beautiful horses and serene farm landscape. Yoga is for everyone and can be done while seated or standing. All abilities are welcome! Farm tours are available following yoga for all interested.
'Knock on Wood' - Artists' Gallery August Reception
August 3rd; Main Street – Old Ellicott City, 2:00pm – 5:00pm
Knock On Wood celebrates the beauty and versatility of wood. The show features the intricate woodcuts of one artist, inspired by nature, landscapes, and animals, alongside the exquisite turned décor and functional art of another. United by their passion for wood and exceptional craftsmanship, both artists present a collection of pieces that explore technique, concept, and material revealing the subtle nuances and striking possibilities within the grain – from the understated to the dramatic.
Glen Burnie Pearls of Service 4th Annual Pier Perfection Day Party
August 3rd; Kurtz’s Beach; Pasadena 3:00pm – 7:00pm
The Glen Burnie Pearls of Service foundation in partnership with Alpha Kappa Alpha Sorority, Incorporated®, Omicron Gamma Omega Chapter are back again with our 4th Annual Seersucker, Sundresses, & Sneakers Day Party at Kurtz Beach. We are excited for summer fun where all proceeds will support scholarships for college students and community services. We’re looking forward to you joining us.
White Marlin Open
August 4th – August 7th; Harbour Island Marina, Ocean City
Get hooked on the action at the White Marlin Open, the world’s largest billfish tournament, returning to Ocean City, Maryland this August! This legendary event draws anglers and spectators from around the globe for a week of high-stakes sport fishing, million-dollar prizes, and serious summertime excitement. Whether you're casting off or just watching the weigh-ins at Harbour Island from 4–9:15 p.m. daily, there's something for everyone. Enjoy the spectacle, shop tournament merch, and be part of one of OC's biggest summer traditions!
National Night Out
August 5th; Crofton Country Club, Gambrills 6:30pm – 8:30pm
National Night Out is an annual community-building campaign that promotes police-community partnerships and neighborhood camaraderie to make our neighborhoods safer, more caring places to live. National Night Out enhances the relationship between neighbors and law enforcement while bringing back a true sense of community. Furthermore, it provides a great opportunity to bring police and neighbors together under positive circumstances. Millions of neighbors take part in National Night Out across thousands of communities from all fifty states, U.S. territories and military bases worldwide on the first Tuesday in August. Neighborhoods host block parties, festivals, parades, cookouts and various other community events with safety demonstrations, seminars, youth events, visits from emergency personnel, exhibits and much, much more.
Summer concert series:
Waugh Wednesdays: Summer Concert Series - - July 30th; Waugh Chapel Town Center: The Eric Scott Trio
Tides & Tunes - July 31st; Annapolis Martime Museum: Timmy Metz Band featuring Tambo
The Fuse: August Summer Concert – August 2nd; The FUSE: Thunder ball
Free Avalon Outdoor Concert Series – August 2nd; Avalon Theatre: Kentavius Jones Band
Bayside Summer Concert Series – August 3rd; Downs park
Allen Pond Summer Concert Series – August 3rd; Allen Pond Park: Lady Da Flame & Friends
Tunesday: Summer Concert Series – August 5th; Back Creek and Second Street Eastport: Jay Crawdads
