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The First Sunday Arts Festival in Annapolis: Where Art Meets the Chesapeake Each Month
On the first Sunday of every month from May through November, more than 150 artists take over the brick streets of historic Annapolis, MD, for a free outdoor market with live music at multiple stages and waterfront dining. No tickets, no admission, just show up.
Event details
On the first Sunday of every month from May through November, West Street and Calvert Street in downtown Annapolis close to traffic and open to something more interesting: more than 150 local and regional artists, food trucks, live acoustic music at multiple performance locations, and the slow, browsing kind of afternoon that makes a waterfront city weekend worth the drive. The First Sunday Arts Festival, organized by the Inner West Street Association and located at the first block of West Street and Calvert Street in Annapolis, Maryland, runs from 11:00 a.m. to 5:00 p.m. each festival Sunday. Admission is free. No tickets required.
The vendor mix at any given edition includes paintings, photography, wheel-thrown pottery, fused and blown glass, handmade jewelry, woodturning, sculpture, fiber arts, candles, and home decor, all sold directly by the makers. Live music plays simultaneously at Stan and Joe’s Lot from 11:00 a.m. to 1:30 p.m. with D’Vibe and Conga, then the Johnson Male Chorus from 1:45 to 2:15 p.m., and Island Breeze from 2:30 to 5:00 p.m. People’s Park and Weisman Park both host additional performers throughout the day. Seven cafe-style restaurants along the festival corridor are open for full sit-down meals, adding a dining dimension that keeps visitors on the street through the afternoon.
Annapolis and the Chesapeake Bay
Annapolis has served as a working port since the 1640s, and the Chesapeake Bay is visible from the City Dock a short walk from the festival corridor. The U.S. Naval Academy grounds, open to the public at Maryland Avenue Gate, occupy the waterfront northeast of downtown and are worth an hour’s exploration before or after the festival. The City Dock, busy with working and recreational boats, gives the festival weekend a maritime texture no inland arts fair can replicate. Ego Alley, the narrow city dock channel alongside the dock, draws spectators year-round as sailboats and powerboats parade past for an informal show that has no admission charge either.
Quick Tips
Free parking is available at Calvert Street Parking Garage at 19 St. Johns Street and Whitmore Parking Garage at 25 Clay Street. The festival is dog-friendly, though the July and August heat can be taxing for pets. Bring a tote bag for purchases. The brick streets are manageable for strollers but uneven in places.
Who Goes and When to Go
This is a strong outing for couples looking for a low-key, high-quality Sunday afternoon, for families with children comfortable with an outdoor crowd, and for anyone already spending the weekend in the Annapolis area. The festival takes on a different theme each month, ending the season in November with a holiday focus. May and October tend to offer the most comfortable weather for a full five-hour visit. Summer months draw larger crowds but also longer vendor days and more music. Each month’s festival is essentially a new event.
Where to Stay Near the Water
The Annapolis waterfront has boutique hotels and bed-and-breakfasts within easy walking distance of the festival zone. For a full weekend on the Chesapeake, look for vacation rentals in the Annapolis area on Lake.com that offer bay views and access to the city’s historic waterfront. May through September books quickly for Annapolis weekends. Secure your stay at least four to six weeks before your chosen festival Sunday.
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