Downtown Annapolis Partnership and Annapolis Art District host the Annapolis Small Business Saturday on the first Saturday after Thanksgiving. With the festive spirits of the holiday season, shop and explore the unique or creative items throughout downtown Annapolis on 29 November 2025. Around 90 retail shops and 80 restaurants are going to participate and welcome locals and visitors for this one-day event. Moreover, you can buy your favorite stuff from an array of vendors in downtown Annapolis. It allows you to appreciate their contribution in flourishing the local economy of the city. Highlighting this special community event in Annapolis, let’s delve into what you will experience at this Small Business Saturday 2025.
Main Attractions of Annapolis Small Business Saturday
- This shopping day at downtown Annapolis is entitled for the local and small business serving the city for decades. Furthermore, it will celebrate the hard work of independent retailers striving to make a mark with the quality of services. Come and explore what premier and unique selections they have in stores for you.
- Attendees will get a chance to unveil the exclusive shopping and dining along Maryland Avenue, Main Street, West Street, State Circle, Market Space, Dock Street, and Randal Street. Savor the delicious food while shopping for the holiday events at downtown Annapolis. No doubt it is one of the best family-friendly getaways to enjoy the holiday celebrations.
- To boot, you can get exciting discounts and deals and gift cards at your favorite shops, allowing you to get many perks. Moreover, special giveaways and sales, from food to artisan markets, Annapolis Small Business Saturday is a can’t-miss holiday celebration.
- In addition, the holiday decorations along different streets in downtown will create a magic stroll as you explore the pop-up. Many vendors will install stalls in streets with amazing budget offers to boost their business and get visibility in the market. Significantly, it is a great opportunity for all independent and local businesses to showcase their products and garner customers.
Underscoring the parking during the event, there are spacious and free parking areas for locals and visitors. For example, Calvert Street Parking Garage and city-owned parking garages offer all-day free parking. However, you have to pay $4 for parking at Whitmore Parking Garage. For more details, you can check all information about parking here.
Read about the Annapolis 2025 Black Friday deals and shopping guide here.