Back to School Community Resource Festival
The Department of Social Services presents the Back to School Community Resource Festival at the Edgewater Library on September 20, 2025 from 11:00 am – 2:00 pm. For more information …
Annapolis Chocolate Binge Festival
The Inner West Street Association brings you the popular Annapolis Chocolate Binge Festival to downtown Annapolis for the holidays. Held on Sunday, December 7, 2025 from 11:00 am to 4:00 …
Harvest Bash: Oktoberfest Edition
Join us for a night of great food, drink, and company in celebration of the season and in support of Providence’s mission. Providence’s Harvest Bash features: Entertainment by the Dan …
Weems & Plath Tent Sale
For over 30 years, Weems & Plath has held this popular, two-week event at our headquarters during the Annapolis Power Boat and Sailboat Shows. This annual sale offers big discounts …
Annapolis Horticulture Society’s Annual Plant Sale
From our gardens to yours, a selection of native and non-native plants that thrive in our climate. The annual AHS Plant Sale is planned for September 6, 2025. It’s held …
BD Provisions Book Club
Don’t miss the BD Provisions Book Club! Come join us for our third book club. We will be reading Little French Bistro by Nina George. If you RSVP that you …
Sip & Shop!
In collaboration with our restaurant, Grapes Wine Bar, we are hosting our Bi-Annual Sip & Shop evening event! Stop by anytime between 4:30 pm – 7:30 pm to shop through …
Trash to Treasures Rummage Sale
Rummage through those closets, basements, and garages. Someone else’s clutter is another’s treasure! Make money at our community-wide Rummage Sale. The Trash to Treasures Rummage Sale will take place at …
Holiday Craft Fair
Earleigh Heights Volunteer Fire Company is hosting our first annual Holiday Craft Fair! We plan to offer unique, handmade holiday gifts, beautiful decorations, and festive fun for all ages.
Oktoberfest
The most anticipated event of the season—Oktoberfest 2025 in West Annapolis!Craft RaR beer will be flowing, provided by our dear friends and neighbors at Chessie’s Wharf. • 100+ amazing vendors• …