Kick off the holiday season downtown by participating in Small Business Saturday! On November 29, celebrate the local shops and businesses that give our community its unique character. From boutique retailers and artisan markets to neighborhood restaurants and cozy cafes, this special weekend encourages everyone to shop local, support small business owners, and discover something new along historic Main Street and beyond. Join fellow Annapolitans in making a difference, enjoy festive decorations, and help ensure that the places you love continue to thrive for years to come.
The City of Annapolis is bringing back its annual holiday parking program, offering visitors and residents expanded free and discounted parking options between Thanksgiving and New Year’s. Downtown metered and kiosk spaces will provide two hours of free parking when using the ParkMobile app, while Mills-Hillman Garage will offer the first hour free through the app, with additional time available at standard rates. City residents enrolled in the “Residents Park Free” program can also enjoy an extra hour of free parking at Mills-Hillman during the promotion.
Additional parking options include the year-round Residents Park Free program at City-owned garages (Gotts, Knighton, Park Place, and Mills-Hillman) and the Park, Shop & Dine validation program, which grants two hours of free parking at participating garages when patrons shop or dine downtown.
The annual Small Business Saturday, which offers a distinctive shopping experience with over 200 local businesses, including 95 retailers and 75 eateries, is scheduled for November 29 in downtown Annapolis. Knock out your holiday shopping and enjoy the quaint holiday ambiance of our little town. Check out just a few stores you can shop downtown.
The Cottage
An Annapolitan staple that is a great place to grab the perfect gift for one of the special women in your life. This charming women-owned boutique at 149 Main Street offers a thoughtfully curated mix of apparel, jewelry, candles, home décor, beauty products, and gifts. For gift-hunters, the ever-changing selection (seasonal scents, trending accessories, kids’ items too) means you’ll likely find something unique each time you stop in. They also have some options available for men. Check out their holiday gift guide for a preview of what they have available. Keep an eye on their Facebook page for their Small Business Saturday deals.
Here. Pop-Up Shop
Running now through December 21, the HERE. Holiday Pop-Up Shop brings together a vibrant, ever-changing collection of goods from local Maryland and Annapolis makers. Packed with clothing, accessories, holiday décor, home décor, prints, self-care items, cards, pet gifts, and so much more, the space is designed for effortless one-stop gifting, whether you’re shopping for your mom, your co-worker, your grandma, your kid, or even your dog. The pop-up celebrates small-batch creativity and hometown pride, offering plenty of Maryland-themed apparel and décor that you won’t find in big-box stores. With new items added throughout the season, it’s a cheerful, high-energy holiday shopping destination perfect for browsing and discovering something unexpected.
Local by Design
Local by Design is a vibrant, community-driven shopping experience that spotlights local artisans and women-owned small businesses. At its downtown Annapolis location (and others in the area) you’ll find everything from artwork, bags, puzzles, and cutting boards to painted furniture, home décor, and accessories. The concept is “shop with intention,” meaning each purchase supports a creator and celebrates craft and locality. Hundreds of makers are featured, and customers enjoy discovering pieces that add creativity and character to their homes or offices.
MADE+
One of downtown Annapolis’ newest additions, MADE+ brings a fresh, hyper-local twist to custom footwear and streetwear. Their bold Maryland-flag designs are already turning heads, offering a perfect blend of state pride and modern style. MADE+ combines craftsmanship, creativity, and local identity, making it an exciting stop for anyone looking to gift (or get) something totally unique and proudly Annapolitan.
Mango and Main
Located on Maryland Avenue, Mango and Main is a bright, inviting boutique dedicated to fair-trade fashion, accessories, and home décor from around the world. The shop partners directly with artisan groups, many women-led, in countries such as Kenya, Guatemala, India, and Haiti, bringing beautifully handcrafted items with meaningful stories behind them. Shoppers will find everything from apparel and bags to jewelry, textiles, and globally inspired home goods, all made with ethical production practices and sustainable materials. Whether you’re picking up a unique gift or adding an eye-catching piece to your own home, Mango and Main offers thoughtful, feel-good shopping with a global footprint and a distinctly local charm.
Old Fox Books
Straight out of a Nancy Meyers movie, Old Fox Books & Coffeehouse at 35 Maryland Avenue is for the book lovers, coffee drinkers and conversational wanderers. Their selection of titles spans new releases, old favorites, and eclectic gems across genres, plus unique stationery and gift items. What’s more, the back-coffeehouse area invites lingering and browsing, making it the perfect spot whether you’re buying your next read or sipping a locally roasted brew while you browse.
The Spice & Tea Exchange
This aromatic, sensory-rich shop at 155 Main Street specializes in gourmet spices, handcrafted seasoning blends, loose-leaf teas, salts, flavored sugars, and kitchen accessories. During the holiday season the store really shines, offering over 85 handmade specialty mixes and plenty of gift-worthy packaging and flavors. Whether you’re shopping for the foodie in your life or looking to add a little spice (literally) to your own kitchen, it offers a rich variety that’s distinctively different from your typical chain offerings. Get a preview of the pre-packaged gifts they have available for the holidays.
Woodcraft Artisans
Woodcraft Artisans has been a fixture in Annapolis since 2009 and specializes in handcrafted wooden décor, most notably three-dimensional wood maps of lakes and coastal areas (over 7,000 designs are available). The store draws fans of nautical style, geographic décor and unique, locally-crafted home or office accents. Whether someone is a Chesapeake Bay-lover, an adventurer, or simply appreciates high-quality woodwork, this shop offers something memorable and conversation-worthy.
As you set out to enjoy Annapolis’ Small Business Saturday, remember that every purchase you make is an investment in the businesses and neighbors who help give our city its welcoming spirit and festive charm. With more than 200 local shops and restaurants offering unique gifts, seasonal treats, and warm hospitality, your support helps to sustain the local community. Don’t forget to take advantage of free and reduced parking, share your favorite finds using #ShopLocalAnnapolis, and join in the holiday magic that makes Main Street and beyond truly special this season.
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