Shop,
Dine, and
Discover
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If you love vintage, Maryland Avenue is the destination for you. You'll find everything from vintage jewelry to mid-century furniture
Evergreen Antiques & True Vintage
Object & Entropy
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Beautiful gallery space filled with ever-changing exhibits.
TPA 360
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Set the mood with a vintage record, a favorite book and a perfect cup of coffee.
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From grab&go to a classic three course, dining on Maryland Ave is always a treat.
Annebeth’s
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Treat yourself or someone special.
Annapolis Pottery
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Nestled between Maryland’s State House and the US Naval Academy, Maryland Avenue features beautiful historic homes and gardens.
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Fall in love with classic coastal home design.
AIA
Tina Colbrook Kitchens
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Brett Life Coach
Official Fitness Maryland
Capistrano
Karen James Studio
Providence Strategies
Edward Jones
Precision Safe Sidewalks
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Welcome to our little corner of Annapolis
Bringing together the best of modern and traditional styles. We are dedicated to sourcing heirloom-quality kitchen and table linens that you’ll enjoy for years to come.
Welcome Home Market
Where the locals come to shop!
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Annebeth's
Find your new favorite treat along with a great selection of wine & beer.
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Mango & Main
Fair Trade Apparel, Accessories and Home Goods
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Evergreen Antiques & True Vintage
Objects from around the world found at the oldest antique shop in Historic Annapolis.
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Jo Fleming Contemporary Art
Curated exhibitions featuring regional artists.
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Rasa
Cold Pressed Juices and Seasonal bites
Maryland Avenue Fall Festival!
Sunday October 19 2025, 10-5 Rain or Shine!
Our Fall Festival is one of the longest-running in our state! Our festivals take place on the first two blocks of Maryland Avenue between State Circle and Cumberland Court.
Vendors receive a 10’ x10’ street space on Maryland Avenue for $100 . Vendors must provide their own tables and tents as needed. Tents must be secured with 40lb weighted bags. Any tent that is not properly weighted down will be asked to be removed. MASCMA is not responsible for any damage or injury caused by wind or improperly installed vendor equipment. Vendors must accept responsibility for any injury or damage caused by their items or equipment.
Food trucks and food vendor spaces are $80. These vendors must supply their Anne Arundel County health permit with their application and have it on their person at the event. NO ALCOHOL may be served on the street without special permitting and with permission from MASCMA.
Food vendors must supply their own trash receptacle for food meant to be consumed on-site and remove their waste at the end of the event.
Events are RAIN OR SHINE and will be canceled via email by 8am the morning of the event should weather conditions be prohibitive. Vendors will be considered for future events should we have to cancel. NO REFUNDS are possible.
Our association reserves the sole right to determine which vendors would be most appropriate for a particular event.