Visit Annapolis & Anne Arundel County has come out with this fantastic list of June events for those of us who are staying local as the summer of 2022 kicks off!
Located in the heart of Maryland, Annapolis & Anne Arundel County is the ideal destination for welcoming summer. Travel is back, and Visit Annapolis & Anne Arundel County (VAAAC) is encouraging everyone to access its more than 500 miles of shoreline to craft their own unique Chesapeake Bay Adventure. On land, events abound, including the largest Pride and Juneteenth parades in Maryland. The U.S. Naval Academy will welcome the class of 2026 on Induction Day (I-Day), and athletes and sports enthusiasts from around the world will converge at the USA BMX East Coast Nationals in Severn, and the Race Across America finish line at Annapolis City Dock
For a more complete listing of June events, festivals, activities, and adventures, getaway seekers are invited to visit the VAAAC website and events calendar at www.VisitAnnapolis.org/Events.
Signature Events
June 4-5 – Annapolis Pride Parade & Festival(Downtown Annapolis): Celebrate one of Maryland’s largest LGBTQIA+ parades and enjoy a festival and events all weekend long.
June 5-12 – Annapolis Arts Week (Destination-wide): The annual celebration supports the diverse talents of the local arts community with events throughout Annapolis & Anne Arundel County.
June 10-12 – USA BMX East Coast Nationals(Severn): Up to 5,000 athletes and their families from around the world are expected to descend upon Severn-Danza Athletic Park to compete in a National BMX sports moto competition.
June 17-18 – Annapolis Juneteenth Celebration(Annapolis): The second annual event commemorating the emancipation of enslaved individuals in the United States kicks off with a ticketed VIP gala on Friday evening, followed by a parade and festival on Saturday. The parade begins at City Dock and wraps up at the Bates Athletic Complex where the celebration continues with live music and entertainment, food, vendors, and fireworks.
June 24-30 – Race Across America (Annapolis & Anne Arundel County): RAAM returns to the shores of the Chesapeake Bay again this year! The 3,000-mile trans-continental event begins in Oceanside, CA and ends at Annapolis City Dock. Participants set out on June 14th and 18th and have 12 days to complete the race. Come cheer on the athletes as they cross the finish line!
June 30 – USNA Induction Day (Annapolis): Roughly 1,200 young men and women from around the world (and their families) report to the U.S. Naval Academy to take their first steps toward becoming “plebes” (freshman).
Local Festivals & Events
June 4-5 – Secret Garden Tour (Downtown Annapolis): The Hammond-Harwood House event features private gardens in Spa View Heights, Annapolis, between Murray Hill and Spa Creek. The gardens featured reflect the goals of the home gardeners: to have a beautiful space filled with flowers, trees, shrubs, grasses, and other garden elements, a space that is a pleasure to live in and an inspiration to work in.
June 11 – The 32nd Annual Strawberry Festival (BWI Airport Region): The Ann Arrundell County Historical Society event at Benson-Hammond House features all your strawberry favorites – wines, jams, shortcake, chocolate covered strawberries – as well as crafts, music, and food trucks.
June 25 – Eastport a Rockin’ (Annapolis): Created to expose local music to a larger audience, Eastport a Rockin’ has been attracting music lovers from around the neighborhood and across the region since 1997. More than 30 bands are slated to perform, keeping local, original music front and center.
Father’s Day Weekend Suggestions
Visit Annapolis & Anne Arundel County has curated a list of weekend activities that make it easy for dad to celebrate Father’s Day solo, with the family, or with the guys. Find out more at www.visitannapolis.org.
June 18 – Great Frogs Winery (Annapolis Area): Enjoy live music by Skribe on the patio, weather permitting. Treat yourself to a self-guided tasting or wine by the bottle or the glass, along with wine-friendly snacks. No cover fees. No reservations required for outdoor seating.
June 18-19 – Golf in Anne Arundel County(Countywide): Chill out with dad over a round of golf this Father’s Day weekend! For the best selection, book early.
June 18-19 – Parasailing, Chesapeake Bay (Chesapeake Bay): Check in and check out with Z Flight Parasail and Watersports. Take in views of historic Annapolis, U.S. Naval Academy, and the Chesapeake Bay from high in the sky. Reservations are strongly encouraged.
June 19 – Live! Casino & Hotel (Arundel Mills): Dave Chappelle at The HALL at Live! Show up for the comedy event of the season and make it a weekend dad will never forget!
June – BWI Trail (BWI Airport Region): If dear old dad is the sporty type, take him and the rest of the crew for an outing on the paved 12-mile bike trail that circles BWI Airport. A parking lot and children’s playground are located at the Thomas A. Dixon Observation Area, 1911 Dorsey Road, Glen Burnie. The best part? It’s FREE!
June – BWI Craft Brewery Trail (Countywide): If you’re looking for a reason to roam – with a designated driver, of course – check out four great breweries within a 30-minute drive along the BWI Craft Brewery trail.
June – Jug Bay Wetlands Sanctuary (Southern Anne Arundel County): If celebrating outdoors with a picnic and hike are right up your alley, consider Jug Bay. Featuring wetlands and a wildlife sanctuary, the park lies on the outer edge of Anne Arundel County at its border with neighboring Prince George’s County.
June – Waterfront Dining and Beach Bars (Countywide): Beach Bars are a staple in Anne Arundel County, and Father’s Day weekend is the perfect time to check them out. Travel by car or boat and nibble your way through fun North County waterfront eateries enjoying Chesapeake Cuisine and/or an Orange Crush while enjoying inspiring waterfront views. For a complete list of waterfront dining options, head to the Visit Annapolis & Anne Arundel County website.
Recurring Seasonal Events
Dinner Under the Stars (Downtown Annapolis): On Wednesday evenings and select Saturdays from May 25 through September 24, the first block of West Street closes to automobile traffic and welcomes visitors to dine and shop al fresco under a canopy of white lights reminiscent of old European cities (weather permitting).
First Sunday Arts Festival (Downtown Annapolis): Every First Sunday of the month from May through November, the first blocks of West and Calvert Streets are filled with streets vendors, performers, musicians and more! The signature event encourages area residents and visitors to shop locally, discover new restaurants, and support the arts (weather permitting).
Farmers Markets (Countywide): Summertime is the perfect time to set your sights on cleaner eating with a trip to our local Farmers Markets. Source organic vegetables and fruit, dairy, meat and poultry, local pies and jams, honey, and so much more!
Thomas Point Shoal Lighthouse Tour (Annapolis): Two-hour tours departing from the Annapolis Maritime Museum at 723 Second Street will be available three times a day most Saturdays from June 4 through October 15. These are the only excursions that also provide access to an interior tour of the National Historic Landmark. Registration is on a first come, first served basis, weather permitting.
Tides & Tunes Concert Series (Annapolis): Held on Thursday evenings from June 16 through August 18, the Annapolis Maritime Museum’s popular concert series includes ten weeks of music – from rock, to folk, to blues – against the incomparable backdrop of the Chesapeake Bay. Concerts are FREE; donations are appreciated. Bring a chair or blanket.
