Anne Arundel County Maryland First Sunday Arts Festival
On the first Sunday of each month from May through November, two downtown Annapolis streets fill with the work of local makers. West Street and Calvert Street, in the heart of the city’s Arts District, become an open-air marketplace where more than one hundred artists and crafters set out pottery, jewelry, wood turnings, clothing, furniture, blown and fused glass, photography and paintings. Live music drifts between the stalls, dancers and street performers work the sidewalks, and café tables and food trucks feed the crowd. There is no gate and no ticket; the festival is free to enter, and the goods on the tables are the point. It runs under the Inner West Street Association, a nonprofit that has worked the same stretch of downtown since nineteen eighty-nine. Its rhythm is what makes it distinct: it returns month after month through the warm half of the year, giving the arts district a regular heartbeat.
About
The First Sunday Arts Festival is a monthly open-air marketplace in downtown Annapolis, Maryland, held on the first Sunday of each month from May through November. Its home is the Arts District, along West Street and Calvert Street between Church Circle and the Westgate Circle area, with activity in People’s Park and Weisman Park. The organiser is the Inner West Street Association, a nonprofit active on the street since nineteen eighty-nine. More than one hundred local and regional artists and crafters sell their work directly to the public, alongside live music, dance, theater and street performance, café dining and food trucks. The hours are eleven in the morning to five in the afternoon, admission is free, and the art, crafts, food and drink on offer are for purchase. The published name forms are “First Sunday Arts Festival” and “First Sunday Arts Festivals”, and the sheet title is printed exactly. Annapolis is the seat of Anne Arundel County and the capital of Maryland, and the festival sits in the city’s walkable historic core, a short stroll from the waterfront.
Quick Facts
| Detail | Information |
| Festival name | First Sunday Arts Festival |
| Host town | Annapolis, Maryland |
| County seat | Annapolis is the seat of Anne Arundel County |
| State capital | Annapolis is the capital of Maryland |
| Venue | West Street and Calvert Street, Arts District, downtown Annapolis |
| Parks | People’s Park and Weisman Park |
| Organiser | Inner West Street Association, a nonprofit active since 1989 |
| Season | First Sunday of each month, May through November |
| Hours | Eleven in the morning to five in the afternoon |
| Admission | Free to enter; art, crafts, food and drink are for purchase |
History
The First Sunday Arts Festival grew out of the work of the Inner West Street Association, the nonprofit that has tended the commercial and cultural life of West Street since nineteen eighty-nine. The association’s purpose has always been practical: to keep the street lively and to support the galleries, theaters, shops and restaurants that line it. A monthly open-air marketplace was the natural expression of that purpose — one Sunday a month through the warm season, so that the district would have a steady pulse rather than a single burst.
No founding year for the festival is stated in the layers read. What the layers do record is the shape the event has settled into: a monthly series, May through November, on the first Sunday, with hours from eleven in the morning to five in the afternoon. The 2026 season listed seven dates, from the third of May through the first of November, and the 2025 season listed editions in June, July, August, September, October and November. The pattern is steady: the festival returns, month after month, and the district’s shops and galleries build their seasons around it.
Annapolis is a small capital city with a compact historic downtown, and West Street is one of its main commercial spines. The festival brings makers and shoppers onto the street together, and the galleries, theaters, shops and restaurants around the stalls benefit from the foot traffic. There is no grand origin story in the record — no single founder, no dramatic first edition — only a working nonprofit, a street that needed life, and a format that has held.
For a useful comparison, see the Anne Arundel County Maryland Annapolis Chocolate Binge Festival for another county festival.
What to Expect
On a festival Sunday, West Street and Calvert Street are given over to stalls. More than one hundred local and regional artists and crafters display pottery and ceramics, jewelry, wood turnings, clothing, furniture, blown and fused glass, photography and paintings. The makers sell directly, so a visitor can ask about a piece and buy from the person who made it. The stalls are the core of the day, and the browsing is unhurried.
Around the stalls, the day has a second layer. Live music plays through the afternoon, dancers and theater performers work the sidewalks, and street performers move through the crowd. Café dining spills onto the pavement, and food trucks add to the choices. People’s Park and Weisman Park give the day breathing room — places to sit, to eat, and to step out of the flow of shoppers. The atmosphere is that of a neighborhood market rather than a fairground: the scale is human, the pace is easy, and the emphasis is on looking, talking and buying from makers.
The festival is free to enter, and every layer read agrees on that point. There is no admission charge at any point in the season. What costs money is what visitors choose to buy: the art and crafts on the stalls, the food and drink from cafés and trucks. A visitor can spend the whole afternoon browsing and listening without spending anything, or can come with a budget for a particular piece of pottery, a print, or a piece of jewelry. The event is an outdoor street market, so the weather shapes the day.
Planning Your Visit
The festival runs from eleven in the morning to five in the afternoon on the first Sunday of each month, May through November, so the first decision is simply which month to attend. Each edition carries the same format — the same streets, the same hours, the same mix of makers, music and food — but the stalls change, because the roster of artists and crafters shifts through the season. A visitor who comes in May will see different work than a visitor who comes in October, and the goods change with the season.
Annapolis is the capital of Maryland and the seat of Anne Arundel County, and its downtown is compact and walkable; the festival streets sit in the Arts District between Church Circle and the Westgate Circle area, a short walk from the waterfront. Parking downtown is limited on festival Sundays, so visitors who arrive early find the easiest parking, and those who come later should expect to walk from a garage or a lot on the edge of downtown. Entry is free, so the budget question is about purchases: bring cash and cards, since makers vary in how they take payment, and plan for food and drink from the cafés and trucks. Comfortable shoes matter, and a bag for purchases is useful, since the stalls sell pottery, glass and framed work that needs carrying.
Because the event repeats monthly, there is no need to squeeze everything into one visit. A first-time visitor might browse the stalls in the morning and listen to music in the parks in the afternoon, and a returning visitor might come with a specific maker in mind. The same streets, a different set of stalls, a new reason to walk them.
Sample Itinerary
Arrive just before eleven in the morning, when the stalls are opening and the street is at its calmest. Start at the Church Circle end of West Street and walk the market slowly, looking at the pottery, jewelry and glass before the crowds thicken. Stop to talk with a maker or two — the direct sale is the point of the day. By midday, find a café table or a food truck for lunch, and take the meal into People’s Park or Weisman Park, where the music carries across the grass.
Spend the early afternoon on the second half of the market, along Calvert Street and back toward the parks, looking at the furniture, wood turnings, photography and paintings you passed over in the morning. Catch a dance or theater performance on the street. In the late afternoon, make the purchases you have been weighing all day, then take a final walk through the Arts District’s galleries and shops. Leave by five in the afternoon, when the stalls close.
Comparison
The First Sunday Arts Festival belongs to a family of street markets and arts festivals, and its closest relatives are the recurring maker markets of the mid-Atlantic, where local artists sell directly to the public on a regular schedule. What sets it apart is its monthly rhythm: most festivals of this kind happen once a year, while this one returns seven times a season, so the relationship between makers and visitors is ongoing rather than annual. The footprint is two streets and two small parks, so the day feels intimate rather than sprawling.
The Annapolis Chocolate Binge Festival, which shares the same organiser and the same street, shows the contrast clearly. That event is a single December Sunday devoted to chocolate, with an admission charge and a narrow theme; the First Sunday Arts Festival is a monthly series with no admission charge and a broad theme. “Annapolis Arts Week”, a destination-wide celebration in June, is a different kind of event again — a week-long, city-wide programme rather than a street market. The First Sunday Arts Festival is the steady one: the same streets, the same hours, the same free entry, month after month.
Checklist
- Check the calendar for the first Sunday of the month, May through November
- Arrive near eleven in the morning for the calmest browsing
- Wear comfortable shoes for a day on foot
- Bring cash and cards, since makers vary in how they take payment
- Carry a bag for pottery, glass and framed work
- Plan lunch from the cafés and food trucks
- Allow time for People’s Park and Weisman Park
- Leave room in the day for the galleries and shops around the market
- Expect downtown parking to fill as the afternoon goes on
- Remember that entry is free and purchases are the only cost
Beyond the Festival
The festival sits in the middle of one of the most walkable historic downtowns in the country, and the day around it is worth the walk. Annapolis is the capital of Maryland and the seat of Anne Arundel County, and its streets carry the state’s history in brick and timber: the state house, the waterfront, the narrow lanes of the historic core. The Arts District’s galleries, theaters, shops and restaurants stay open around the festival, and a visitor who comes for the stalls can spend the rest of the day on the waterfront, in the shops, or in a gallery.
People’s Park and Weisman Park give the market its green edges, and they are where the music is heard most clearly and where families settle for the afternoon. The goods on the stalls in May are not the goods on the stalls in October, and a visitor who returns through the year sees the same streets in different moods.
Significance
The First Sunday Arts Festival matters because it is steady. A single annual festival can transform a town for a weekend and then vanish; a monthly market changes the town more slowly and more lastingly, by giving makers a regular place to sell and giving the district a regular reason for people to come downtown. The Inner West Street Association has worked West Street since nineteen eighty-nine, and the festival is the most visible expression of that work: a nonprofit, a street, and a roster of more than one hundred artists and crafters, meeting on the first Sunday of the month through the warm half of the year. The event supports the galleries, theaters, shops and restaurants around it without charging admission. In a small capital city whose downtown depends on foot traffic, that steady, free, monthly gathering is a piece of civic infrastructure as much as a festival.
Frequently Asked Questions
Which months does the First Sunday Arts Festival run?
The festival runs on the first Sunday of each month from May through November, eleven in the morning to five in the afternoon. The 2026 season ran from the third of May through the first of November.
What kinds of work do the makers sell?
More than one hundred local and regional artists and crafters sell pottery, jewelry, wood turnings, clothing, furniture, blown and fused glass, photography and paintings, with live music, dance, theater, street performance, café dining and food trucks alongside.
Does it cost anything to enter the festival?
No. Admission is free, per every layer read. The art, crafts, food and drink on the stalls and at the cafés and trucks are for purchase, so visitors spend only on what they choose to buy.
Where exactly does the market take place in Annapolis?
West Street and Calvert Street in downtown Annapolis, in the Arts District between Church Circle and the Westgate Circle area, with activity in People’s Park and Weisman Park. Annapolis is the seat of Anne Arundel County and the capital of Maryland.
What to Expect From the Next Anne Arundel County Maryland First Sunday Arts Festival
How often is Anne Arundel County Maryland First Sunday Arts Festival held?
The festival is a monthly series, held on the first Sunday of each month from May through November — seven editions in the 2026 season, and editions in June through November in 2025.
When is the next Anne Arundel County Maryland First Sunday Arts Festival?
The next edition falls on the first Sunday of the next month in the May-through-November season, eleven in the morning to five in the afternoon, on West Street and Calvert Street in downtown Annapolis.
Will the dates change?
The festival’s dates follow a fixed pattern — the first Sunday of each month, May through November — so the calendar dates shift with the month while the pattern stays the same. A visitor planning ahead should check the month’s first Sunday rather than a fixed date.
The First Sunday Arts Festival is a small, steady pleasure: a free monthly market on two downtown streets, where more than one hundred makers sell their work directly and music plays through the afternoon. It returns on the first Sunday of the month, May through November, and it is worth returning with it.
