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FENWICK STREET connects Route 5 to Washington Street at the heart of downtown Leonardtown, but visitors will want to explore the collection of eclectic shops and enjoy the vibrant energy and hip vibe of the main part of this street right off of Leonardtown Square. In this short block, visitors can take in an art show at the local art gallery, explore a bookstore with a maze of isles and fun reading nooks, have a coffee or a glass of wine at a coffeeshop that used to be an authentic speakeasy that was originally nestled behind a bookcase, spend an evening at an art studio with friends where you each choose anything from boards to clocks to distress, decorate with stain, paint and leave with a piece of art to take home. Soon to host Block Parties, Fenwick Street is quickly becoming an exciting, must see (and experience) district in historic Leonardtown. View images below and learn about the businesses along Fenwick Street below.



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Browse and shop fine art and gifts, attend art shows, exhibits and special events like the monthly First Friday Art & Wine Date Nights at the North End Gallery

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Browse and shop books, records and games and attend special events like book signings, tarot card readings, artist meet-and-greets and more


Visit Social, a neighborhood coffeehouse and cocktail bar for mouth-watering espresso, smoothies, specialty cocktails, light fare and tapas. Social frequently hosts movie nights, live acoustic music and parties

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Attend a special event or party at the Fenwick Inn, an elegant event space featuring a beautifully restored indoor party area and outdoor pavilion. Sample events include cookie decorating, flower arranging, farm-to-table dinners and more. The Fenwick Inn is also available to book your own parties and special events.


Book a DIY board decorating workshop at Board & Brush. Gather friends and family and make it a party.

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Book a sip and paint workshop or party with friends at the Wine & Design Studio. Choose your project and create your very own work of art.
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