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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Lovingly curated apparel and accessories
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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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Bloom Luxury Box
Yessica Perez is the owner and head floral designer of Bloom Luxury Box. Yessica and her team will uniquely create special and personal arrangements that will fit your needs and your budget for every occasion.
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Harry Brown's
Classic dining for that special occasion or a gourmet pizza to-go, Harry Brown’s is a landmark.
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Cezanne Jewelers
You’ll fall in love with the beautiful jewelry and keep coming back for the incredible personalized service
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Evergreen Antiques & True Vintage
You’ll fall in love with this collection of vintage jewelry, apparel and furniture. A new discovery around every corner.
Welcome
to our little corner of Annapolis
Feel the Love on Maryland Avenue!
You’ll find the perfect gift for your Valentine from the classic Flowers & Chocolates to a piece of Vintage Jewelry.
XOXO Maryland Avenue
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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Galway Bay Irish Pub & Restaurant
Come for the Guinness and stay for the generous hospitality and fantastic comfort food!
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Jo Fleming Contemporary Art
Curated exhibitions featuring regional artists.
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Groundswell Yoga
Not just any yoga studio. we are a community deeply committed to sweat and soul. and when we practice together, we become better versions of ourselves.
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.