What’s Up Media’s Best of Party 2026
What’s Up? Media’s Best Of Party celebrates the best of the area’s restaurants, shops, services, entertainment, and businesses all rolled up into one fantastic fundraising event supporting Charting Careers.
10 events found.
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*Please note – While we make every effort to crosscheck links and event details, we always encourage you to do the same before making final plans. If details are missing or incorrect, please let us know so that we can correct them. Thanks for your help!
Events
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Doordan Institute 2000 Medical Parkway, Annapolis
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Naptown Social Stroll
Citrus Bros West StIf you're looking for a fun, low-key way to get outside, meet people, and explore Annapolis, the Naptown Social Strolls are exactly what they sound like — and then some. […]
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Tunesday | A Floating Concert Series
Back Creek 655 Americana Dr, Annapolis, United StatesEvery Tuesday night, 90 minutes before sunset. No fixed clock time, just show up before the light gets golden and you’re good.
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Carnival – Annapolis Mall
Westfield Annapolis Mall 2002 Annapolis Mall Rd, Annapolis, MD, United StatesCome and discover the excitement at the largest carnival in town, happening from June 4 to June 14, 2026 at Annapolis Mall, Annapolis, MD! Brace yourself for heart-racing rides, fun […]
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Fairy House Festival
Quiet Waters Park 600 Quiet Waters Park Road, Annapolis, MD, United StatesFairy-inspired costumes are welcome and encouraged!
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The Resin Room DIY Glass + Wood Resin Art
The Resin Room 209 West Street, Annapolis, United StatesDIY Workshops in Glass & Wood Resin Art. Wed-Sun, various times. By appointment - Book Online.
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Homestead Gardens Beer Farm
Homestead Gardens - Davidsonville 743 W Central Ave, Davidsonville, MD, United StatesOur state-of-the-art ten-barrel brewery and inviting TapRoom, featuring both indoor and outdoor seating, provide the perfect setting for relaxation and connection.
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Food Truck Wednesdays on the Farm
Food Truck Wednesdays on the Farm 8401 Veterans Highway, Millersville, United StatesEnjoy rotating food trucks, family-friendly farm vibes, come hungry + bring the family!
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FREE Car Show + Live Music
The Boathouse at Anchored Inn 604 Cabana Blvd, Deale, United StatesBring your classic, hot rod, muscle car, truck, motorcycle — or just come walk around and check them all out. Live music: 5–8 PM!
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Paca Girlfriends Party 2026
William Paca House and Garden 186 Prince George St, Annapolis, MD, United StatesShop in our festive marketplace, meet and greet with local designers, and connect with a wide network of influential women.