Annapolis First Sunday Arts Festival: Getting There Guide

The Annapolis First Sunday Arts Festival is a free outdoor art market held the first Sunday of every month from May through November on West Street and Calvert Street in downtown Annapolis, Maryland. The October 2026 edition falls on Sunday, October 4, running from 11:00 AM to 5:00 PM. More than 150 local and regional artists display original artwork, handmade crafts, photography, pottery, jewelry, glass, woodwork, and fiber arts alongside food trucks, live music at multiple stages, and café dining at seven West Street restaurants.

Annapolis First Sunday Arts Festival 2026 — Event Details

The festival is organized by the Inner West Street Association and takes place in the Annapolis Arts District. The selection committee curates the vendor mix — only original artwork, photography, handmade jewelry, handmade crafts, creative literary arts, antiques, and vintage items are allowed. Mass-produced goods are excluded.

What to Expect at the Arts Festival

The range of media is broad: paintings, photography, wheel-thrown pottery, fused and blown glass, jewelry, woodturning, sculpture, fiber arts, candles, home décor, and more. Prices range from affordable impulse buys to gallery-quality pieces. Multiple performance locations host live music throughout the day — Stan and Joe's lot (11 AM–5 PM), People's Park (noon–5 PM), and Weisman Park. Food trucks line the festival route, and seven West Street restaurants offer outdoor café dining.

How to Get to the Annapolis Arts District

Parking in Downtown Annapolis

Calvert Street Parking Garage (19 St. Johns Street) is the closest large structure, directly adjacent to the West Street corridor. Whitmore Parking Garage (25 Clay Street) is a second option within walking distance. Street parking fills quickly on festival Sundays — the garages are the most reliable option. The Annapolis Transit Gold Route also serves the West Street corridor.

Why Groups Choose a Vehicle for the Arts Festival

For groups of 4 or more from Baltimore, DC, or the Maryland suburbs, a chauffeured car service simplifies the logistics. Downtown Annapolis parking on a busy Sunday is competitive — garages fill and street spots are scarce. A dedicated vehicle drops the group at West Street and picks everyone up when the browsing is done. This is especially practical for groups combining the festival with a waterfront lunch, a walk through the historic district, or dinner at City Dock — a group vehicle connects all the stops without parking twice.

Why Group Transportation Makes Sense in Annapolis

For four or more people, coordinating several cars can quickly become inconvenient in downtown Annapolis. Drivers have to find parking, keep track of where each vehicle is parked, and coordinate with the rest of the group when it is time to move to the next stop. A chauffeured vehicle keeps everyone together and allows the group to focus on the festival rather than navigating between parking areas.

This can be particularly helpful for visitors coming from Baltimore, Washington, DC, Columbia, and other Maryland suburbs. Instead of having each person drive separately into Annapolis, the group can arrange a central pickup and travel together. The same vehicle can then remain available for the return trip after the day's activities are finished.

Combine the Festival With an Annapolis Day Out

The festival can easily become part of a longer Annapolis itinerary. After browsing the event, groups can continue toward the waterfront for lunch, explore the historic district, or spend time around City Dock before heading to dinner. Having one vehicle for the day makes it easier to move between these stops without repeatedly looking for parking or asking everyone to meet at a new location.

For families and groups of friends, this flexibility can make the schedule feel less rushed. The group can decide how long to stay at the festival and adjust the rest of the afternoon around the day's plans. A dedicated vehicle also gives visitors coming from outside Annapolis a convenient way to see more of the city during the same trip.

Plan Your Pickup and Return Trip

Before heading to the festival, establish where the group will be picked up and where the vehicle will meet everyone afterward. This is especially useful when several people are visiting different parts of downtown Annapolis during the day. Rather than trying to locate a parked car after the event, everyone can return to an agreed pickup point and leave together.

For groups traveling from Baltimore, DC, or the Maryland suburbs, arranging the return transportation in advance also removes one more decision from the end of the day. Whether the itinerary ends at City Dock, a restaurant, a hotel, or back at the original pickup location, having the transportation plan established beforehand keeps the group on the same schedule.

Making It a Full Annapolis Day

1. Before the Festival (9–11 AM)Coffee and breakfast on Main Street or West Street. Historic district restaurants open well before 11 AM.
2. The Festival (11 AM–5 PM)Browse 150+ vendors, eat from food trucks, listen to live music at multiple stages, and visit the seven participating West Street restaurants.
3. After the FestivalWalk to City Dock and the Annapolis waterfront (10-minute walk east). Outdoor seating overlooking the harbor — the natural end-of-day destination.

Frequently Asked Questions