For some Sundays in July through November, come to the First Sunday Arts Festival which held at the heart of Annapolis for a day of art, music, food, and community.
• Event: First Sunday Arts Festival
• Dates: July 6, August 3, September 7, October 5, and November 2, 2025
• Time: 11:00 AM – 5:00 PM
• Admission: Free
About First Sunday Arts Festival
This is one of the liveliest outdoor art markets in Annapolis. It happens on the first Sunday of every month, from May to November. This event is open to everyone and is a great chance to shop locally, support local artists, enjoy live music, and learn more about Annapolis’s unique charm.
The event takes place on West Street and Calvert Street, in the Annapolis Arts District and historic downtown. It has a lively scene with art, music, and food. Local restaurants serve a wide range of Maryland favorites and other tasty foods, and live music makes the atmosphere even more fun.
Want to be a part of it? Artists and vendors can apply for First Sunday Arts Festival to showcase their work and connect with thousands of visitors.
2026 Festival Music and Entertainment
During the event, you can see live performances at places like Stan and Joe’s Lot, People’s Park, and Weisman Park. Here is the monthly schedule:
May 4
Stan and Joe’s Lot
• 11:00 AM – 1:30 PM: D’Vibe and Conga
• 1:45 PM – 2:15 PM: Johnson Male Chorus
• 2:30 PM – 5:00 PM: Island Breeze
People’s Park
• 12:00 PM – 5:00 PM: Class Act Performing Arts, PJ & Neal
Weisman Park
• Featured Performer: Michael Kocher
June 1
Stan and Joe’s Lot
• 11:00 AM – 1:30 PM: Spirit of Jazz featuring Geno Marriott
• 1:45 PM – 2:15 PM: Johnson Male Chorus
• 2:30 PM – 5:00 PM: Fast Eddie and the Slowpokes
People’s Park
• 12:00 PM – 5:00 PM: Naptown Sings and Plays, Aaron Hawkins
Weisman Park
• Featured Performer: Michael Kocher
July 6
Stan and Joe’s Lot
• 11:00 AM – 1:30 PM: Groove Spot Band and Show
• 1:45 PM – 2:15 PM: Johnson Male Chorus
• 2:30 PM – 5:00 PM: Island Breeze
People’s Park
• 12:00 PM – 5:00 PM: Garrett Park Music (Performers TBD)
Weisman Park
• Featured Performer: Michael Kocher
August 3
Stan and Joe’s Lot
• 11:00 AM – 1:30 PM: D’Vibe and Conga
• 1:45 PM – 2:15 PM: Johnson Male Chorus
• 2:30 PM – 5:00 PM: Spice Band
People’s Park
• 12:00 PM – 5:00 PM: Garrett Park Music, PJ & Neal
Weisman Park
• Featured Performer: Michael Kocher
September 7
Stan and Joe’s Lot
• 11:00 AM – 1:30 PM: Soul Journers
• 1:45 PM – 2:15 PM: Johnson Male Chorus
• 2:30 PM – 5:00 PM: Groove Spot Band and Show
People’s Park
• 12:00 PM – 5:00 PM: Aaron Hawkins (Additional acts TBD)
Weisman Park
• Featured Performer: Michael Kocher
October 5
Stan and Joe’s Lot
• 11:00 AM – 1:30 PM: Performer TBD
• 1:45 PM – 2:15 PM: Johnson Male Chorus
• 2:30 PM – 5:00 PM: Mac Heat
People’s Park
• 12:00 PM – 5:00 PM: Class Act Performing Arts (Additional acts TBD)
Weisman Park
• Featured Performer: Michael Kocher
• 2:00 PM: Rising Stars from Apex Arts
November 2 – Holiday Market
Stan and Joe’s Lot
• 11:30 AM – 1:00 PM: Guava Jelly
• 1:45 PM – 2:15 PM: Surprise Guests
• 2:30 PM – 5:00 PM: Juliet Lloyd
People’s Park
• 12:00 PM – 5:00 PM: Naptown Sings and Plays, Old Mill Steel Drum
Weisman Park
• Featured Performer: Michael Kocher
Every month from May to November, the First Sunday Arts Festival takes place on the streets of Annapolis, Maryland. It is free and open to the public. The festival turns West Street and the areas around it into a lively open-air market and cultural hub every first Sunday of the month.
Local and area artists, singers, dancers, and food sellers will be at this family-friendly event. People can buy fine art, jewelry, pottery, photography, home decor, and other homemade products directly from the artists. Street performances and live music make the atmosphere joyful while surrounding restaurants provide a variety of cuisine.
What is First Sunday Arts Festival?
Arrive Early for the Best Selection
People who sell arts and crafts reach there early, and the most desired things usually sell out quickly. If you reach there at the opening time (11:00 AM), you can choose from the unique, handmade items first.
Wear Comfortable Shoes
The event takes place on several blocks of West Street and in the areas around it, so be ready to walk. If you want to look at booths, walk down side streets, and watch shows, you must wear shoes that are comfortable.
Plan for Parking
You can park your car close at the Calvert Street Garage (19 St. Johns Street) or the Whitmore Garage (25 Clay Street). During the event, Calvert Street is closed, so if you are parking at Gotts Garage, use Northwest Street to get in.
Bring Cash and Cards
Most sellers take credit and debit cards, but it is still a good idea to bring cash with you, especially for small purchases, tipping artists, or in case your link drops.
Don’t Miss the Live Music
Stan and Joe’s Lot, People’s Park, and Weisman Park all have live acts every month. Check the regular list of these Annapolis events at First Sunday Arts Festival and make plans to see your favorite performances.
Explore Local Dining Options
Restaurants on West Street serve food from all over the world, as well as seafood from Maryland. Rest and have a meal or buy street food.
Support Local Artists
If you have the chance, talk to the artists and learn about their work. Also, buy one-of-a-kind art and homemade goods to support small businesses.
Stay Hydrated & Weather-Ready
Dress appropriately for the weather and bring a water bottle. It might rain, so bring an umbrella or raincoat. The show will happen, rain or shine.
Bring the Whole Family
Visitors of all ages can enjoy this event, which is good for families. There may be shows or games in some places that kids will love.
Come Back Each Month
Every event is different because the artists, sellers, and performances change every month. So, try to go there every month!
Where To Stay In Annapolis For First Sunday Arts Festival?
Are you going to stay the night or over the weekend for the First Sunday Arts Festival? Annapolis has several hotels within walking distance of the festival grounds on West Street and in the historic area. To fit any type of trip, here are some of the best choices:
1. Historic Inns of Annapolis
Location: Downtown Annapolis
Why Stay: There are cute, vintage houses right next to the festival and the water. Offers both old-style and modern comforts.
2. Graduate Annapolis
Location: West Street, close to the festival area
Why Stay: The hotel is stylish and artsy, and the rooms are pet-friendly. It is easy to walk to the festival and nearby restaurants.
3. Hilton Garden Inn Annapolis Downtown
Location: West Street
Why Stay: It has modern amenities and is close to the festival’s center. Great for both families and people traveling alone.
4. The Westin Annapolis
Location: West Street
Why Stay: The rooms are nice, and there are relaxing services. A short walk from the festival, places to eat, and stores.
5. 134 Prince – Luxury Boutique Hotel
Location: Historic District
Why Stay: It is a small hotel with a mix of history and high-end service that makes for a luxury and personal stay.
6. Local Bed & Breakfasts
You can stay in a cozy and private B&B in the historic area at Flag House Inn, Annapolis Waterfront Hotel, or Gibson’s Lodgings.