Galentines Day

It’s our fourth Galentine’s Celebration on Maryland Avenue and we look forward to it every year! Grab your besties and head to the avenue for a celebration of the friendships that sustain us every day.

Participating shops have a variety of treats and extras planned for this special evening. Take part in a “2 for 1” yoga class with your Galentine at Groundswell Yoga. Get matching permanent bracelets with your Galentine at Mango&Main. Lastly, sip a sparkly cocktail at Cupla. Stop along the way for a sweet treat and make a new friend or two!

Maryland Day

March 21, 2026 Join more than 50 partners as they host special events, programs and activities that showcase local museums, historic buildings, heritage sites, art galleries, natural resources, archaeological sites, parks, trails and historic communities throughout the Chesapeake Crossroads Heritage Area.

May Day

Every Year on May 1st the residents and shops throughout Annapolis celebrate the arrival of spring with baskets of flowers that can be as simple as a few stems in a basket to elaborate displays that reflect their unique interpretation of a May Basket.

It is a showstopper of a day in Annapolis and a great opportunity to throw on your best sundress and walk the historic streets of Annapolis and marvel at the beauty and creativity all around.

Shop,

Dine, and

Discover

  • 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.

    Read Bio

  • 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

    Read Bio

  • Evergreen Antiques & True Vintage

    You’ll fall in love with this collection of vintage jewelry, apparel and furniture. A new discovery around every corner.

    Click Here

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.

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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.