Shop Local! Shop Downtown Annapolis
Small Business Saturday has become an annual event for our downtown Annapolis business districts. It has been over 11 years since we started celebrating our small local businesses on this …
Midnight Madness
A Festive Shopping time in Downtown Annapolis The first two Thursdays of December from 4 pm until Midnight and the third Thursday of December from 4 pm until 11 …
FALL FEST ON WEST
October 21st Saturday from 2pm to 5pm enjoy live music, pumpkins, kids’ events, outdoor dining and more on West Street in Historic Annapolis followed up with Dinner Under the Stars 5-9pm …
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 December 3rd from 11am to 5 pm on the …
First Sunday Arts Festival
Inner West Street Association is the proud sponsor of Maryland’s premier art festival. From May through November, thousands of visitors enjoy shopping along beautiful West Street in downtown historic Annapolis. …
First Sunday Arts Festival
Inner West Street Association is the proud sponsor of Maryland’s premier art festival. From May through November, thousands of visitors enjoy shopping along beautiful West Street in downtown historic Annapolis. …
First Sunday Arts Festival
Inner West Street Association is the proud sponsor of Maryland’s premier art festival. From May through November, thousands of visitors enjoy shopping along beautiful West Street in downtown historic Annapolis. …
Eastport Yacht Club Lights Parade
It’s a beloved Annapolis tradition! Every year on the second Saturday in December, magic happens on the water of the Annapolis Harbor—boats suddenly appear out of the cold winter night …
Bay Bridge Run
UNIQUELY FUN & CONVENIENT The 10K course will traverse the eastbound span of the bridge from Anne Arundel County to Kent Island in Queen Anne’s County and finish with a …
Annapolis Spring Sailboat Show
The Annapolis Spring Sailboat Show returns to the historic seaport town of Annapolis every April to showcase new and brokerage boats including catamarans, monohulls, family cruisers, daysailers, and inflatables. While …