Fashion for a Cause
A perennial favorite, Annapolis’ premier fashion celebration returns to the U.S. Naval Academy’s Fluegel Alumni Center. This red-carpet event spotlights the season’s best looks, with community models showcasing summer 2026 …
Bags & Beyond Bingo
Get ready for Bags & Beyond Bingo, a fun-filled, family-friendly fundraiser hosted by the Pasadena Elementary School PTA! Join us for an exciting night of bingo featuring designer handbags and …
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 …
Polar Bear Plunge with Rams Head
Join our team for the 30th annual Polar Bear Plunge. Since 2008, Rams Head has been a proud supporter of Special Olympics Maryland’s mission to raise funds and awareness for …
Black Tie & Diamonds
Don’t miss Black Tie & Diamonds! Join us for our annual fundraiser as we support empowering women through recovery with Chrysalis House! This event will take place at Graduate Hotel.
FASO Dine to Donate
Join Friends of Annapolis Symphony Orchestra (FASO) at Luna Blu for a spectacular dinner in downtown Annapolis. All proceeds benefit ASO and ASA. This event is open to FASO members …
Polar Bear Plunge
Join us again this year for the Polar Bear Plunge. Make sure you sign up here to join us on Mr. Peanuts Frozen Challenge Team. The Polar Bear Plunge will take …
Maggie’s Music Extravaganza
Come celebrate and enjoy this Celtic Music reunion concert! It will feature Maggie’s Music Artists. Part of the proceeds will go to support Parkinson’s disease. Maggie’s Music Extravaganza will be …
2026 Winter Island 5K & 10K
Don’t miss the 2026 Winter Island 5K & 10K! It will take place on January 18, 2026 from 8:30 am to 11:00 am at Matapeake Park. Register here!