There’s something about fall and cooler weather that makes us want to shop local. You just can’t beat waking up early on a weekend morning, walking around with a coffee, and browsing handmade pumpkin-scented candles, jewelry, and home décor.
Whatever your reason, grab your reusable shopping bag! From outdoor markets in downtown Annapolis to school craft fairs packed with hundreds of vendors, there are plenty of opportunities to shop small, support local makers, and maybe even get a head start on that holiday shopping list.
Here are the fall and holiday markets and craft fairs happening in and around Annapolis this year.
First Sunday Arts Festival
Oct. 4 & Nov. 1 | West Street, Annapolis
If you haven’t made it to First Sunday yet this year, fall gives you two more chances! Downtown Annapolis turns into an outdoor arts market filled with artists and makers. Stroll along West Street, browse for something you definitely feel like you need, and make a day of it with food, and live entertainment.
Naptown Flea
Oct. 4, 10 a.m.-4 p.m. | MRE Mercantile, Eastport
Naptown Flea is heading to Eastport! Shop more than 20 local vintage sellers, small businesses, and creators for everything from secondhand finds to locally made goods. There will also be an Eastport scavenger hunt encouraging shoppers to explore and support other neighborhood businesses while they’re out.
Fall Vendor Craft Fair
Oct. 10, 9 a.m.-2 p.m. | Glen Burnie Elks Lodge #2266, Severn
More than 40 local vendors in one place? Better clear some room in the trunk. This fall craft fair will feature handmade crafts, home décor, baked goods, custom gifts, woodworking, crochet items, jams and jellies, children’s clothing, and more. Translation: You could knock out some early holiday shopping and come home with something for yourself.
Holiday Craft Fair
Oct. 18, 10 a.m.-3 p.m. | Earleigh Heights Volunteer Fire Company, Severna Park
Yes, we know it’s October, but there’s no rule saying you have to wait until Thanksgiving to start holiday shopping! Head to Earleigh Heights Volunteer Fire Company for another chance to browse local vendors and get an early start on checking names off your gift list.
Maryland Avenue Fall Festival
Oct. 18, 10 a.m.-5 p.m. | Maryland Avenue & State Circle, Annapolis
Shopping with a side of that beautiful fall in Annapolis landscape? Yes, please. The annual festival returns with vendors, food, live music, and drinks. Plus, you’ll already be surrounded by the shops and restaurants of Maryland Avenue and State Circle, so there are plenty of excuses to keep browsing after the festival.
Anchors & Artisans
Oct. 18 | Annapolis Town Center
Make it a market-hopping Sunday! This outdoor pop-up brings local makers and artisans to Annapolis Town Center. Browse the market, grab something to eat, and enjoy a fall afternoon at the Town Center.
Wellsview Community Market
Oct. 25 & Nov. 22 | Wellsview Cottage, Annapolis
Keep your shopping close to home at this monthly Sunday market on Ridgely Avenue. With indoor and outdoor vendor spaces, it’s another opportunity to discover local businesses and makers.
Northeast High School Fall Craft Fair
Nov. 7, 10 a.m.-2 p.m. | Northeast High School, Pasadena
Get a jump-start on that holiday shopping list while supporting Northeast High School! The annual craft fair brings together handmade crafts, gifts, holiday décor, boutique items, baked goods, and more. The fundraiser supports Northeast High School students and PTSA programs, so you can tell yourself that thirteenth wreath you bought was to support the kids!
Pasadena United Methodist Church Annual Craft Fair
Nov. 7, 9 a.m.-2 p.m. | Pasadena United Methodist Church, Pasadena
Craft vendors AND homemade soup? Say less. The annual craft fair returns with local craft vendors and homemade soup.
Early Christmas Fall Flea Market & Craft Fair
Nov. 7, 8 a.m.-3 p.m. | Benson-Hammond House, Linthicum Heights
If you like your craft fairs with a little treasure hunting mixed in, add this one to the list! Hosted at the historic Benson-Hammond House, it’s part flea market, part craft fair, and another chance to shop before the holiday rush really begins.
St. Martin’s Christmas Mart
Nov. 14, 9 a.m.-2 p.m. | St. Martin’s-in-the-Field Episcopal Church, Severna Park
Christmas shopping officially starts NOW! This Severna Park tradition features local artisans and handmade arts and crafts. Even better, proceeds support the church’s community and outreach projects.
Chesapeake High School Fall Craft Fair
Nov. 14, 10 a.m.-3 p.m. | Chesapeake High School, Pasadena
This one is BIG. The annual craft fair brings together more than 270 local artisans with handmade goods and unique gifts. Hosted by the Chesapeake High School Band Boosters, the event benefits the school’s marching band.
Jingle Bell Bargains & Holiday Vendor Market
Nov. 14, 9 a.m.-2 p.m. | Walnut Hill Farm, Davidsonville
Craft market meets Christmas yard sale! Shop local makers AND hunt for gently used Christmas décor and other holiday bargains. There will also be food trucks, live music, and an appearance from Santa himself.
Shop Small This Season!
Whether you’re searching for a handmade gift, something new for the house or just an excuse to wander around with a hot coffee on a crisp fall afternoon, these markets and craft fairs make it easy to support local artists, makers, schools and small businesses.
And let’s be real: “I found it from a local maker at this cute little craft fair” sounds a whole lot better than “I panic-ordered it two days before Christmas.”
Event dates and details can change. Be sure to check with organizers before heading out.
Stay tuned for November when we’ll release our holiday craft fair and market guide.
This is just a roundup of a few spots we know and love — not a complete list of every option out there. There are always more great places to discover!
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