Naptown Vinyl Record Show & Vintage Market
Hosted by Maryland Hall, Naptown Vinyl & Vintage is Annapolis’ premier record shopping opportunity. Come dig through hundreds of crates to find that hidden gem you have been looking for. The …
Barktoberfest
Who let the dogs out, again?! Join us for the third Barktoberfest with steins and canines as we celebrate German-style beer, bavarian food, and pawesome four-legged friends. Get your tickets …
Bourbonanza
Don’t miss Bourbonanza! This is an unlimited sampling event. Only ticketed guests will be admitted. 30+ bourbons to sample including: Bourbon cocktails Blind taste tests Bourbon Tail Mix Snack Bar …
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 …
Taste of Fall on West Street
Fall is in the air on Annapolis’ historic West Street. On Sunday, November 9, 2025 from 2:00 pm – 5:00 pm, join us for a fun community dining event. Enjoy …
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• …
Custom Cars, Cocktails & Change Gala
For over 25 years, Vehicles for Change has been a lifeline for families and individuals seeking a way forward. We believe in second chances and stable transportation. We believe in …
You Had Me At Merlot Book Club
Join us for hot drinks and enjoy even hotter reads in our romance book club! September’s book is Phantasma, by Kaylie Smith. The You Had Me At Merlot Book Club will …
Colonial Cocktails: Literary Libations
Come drink hot buttered rum and gluhwein (mulled wine), two seasonal favorites as together we decide the fate of Tom Jones, a ne’er do well from Henry Fielding’s 1749 novel, …
Women, Wine & Wisdom: Estate Planning
Join us for an empowering evening created exclusively for women located in our Annapolis location, offering a welcoming and supportive space to explore all things finance. Relax, sip on wine, …