Chocolate Crawl
Grab your besties, lace up your comfiest walking shoes, and get ready to sip, snack, shop, and swoon your way through downtown Annapolis. During the Annapolis Chocolate Crawl, participating boutiques …
Healthy Lunch Options in Annapolis
Feeling like your mornings are a sprint you didn’t train for? Stressed about packing a lunch you’ll actually want to eat? Already negotiating with yourself about that 3 PM caffeine …
Bull, Pig, and Oyster Roast
Don’t miss the Bull, Pig, and Oyster Roast! Please join us for an evening full of food, friends, and fun! This event will take place at the Earleigh Heights Volunteer …
Tea & Trivia: Bridgerton Style
Get ready to sip and spill some tea and test your Bridgerton knowledge in this fun trivia event. Period costumes encouraged! Join us for a Regency inspired afternoon tea, Bridgerton …
Paca Girlfriends Party
Wander the picturesque William Paca Garden as you enjoy a glass of bubbly and indulge in culinary creations prepared by the area’s premier chefs. Shop in our festive marketplace, meet …
20th Annual SOUPer Bowl Lunch for the Light House
On February 8, just before two teams face off in a “super” NFL championship game, volunteers in Annapolis will kick off their own SOUPer Bowl, a donation-only lunch to support …
Galentine’s Day Brunch
Celebrate the power of women supporting women at this year’s Galentine’s Day Brunch! Join the Junior League of Annapolis for a morning of joy, connection, and inspiration as we gather …
St. Michaels ChocolateFest
Indulge in the sweetest weekend of the year! The 8th annual St. Michaels ChocolateFest returns on Saturday, March 7, 2026, inviting chocolate lovers from near and far to savor an unforgettable day of …
Herald Harbor Chili Cookoff
Join us for the 2026 Herald Harbor Chili Cookoff, a fun filled winter event bringing neighbors together for great food and community spirit! Proceeds will support ongoing Herald Harbor Citizens’ …
Zero Alcohol, All Flavor: Mocktails in Annapolis
The mocktail scene has really caught on in recent years. They’re not just for pregnant people anymore, either. Anyone can choose to have a good time without the high alcohol …