West Street is the uptown, hipster area of Annapolis, known for art galleries and its music scene.
It’s about a 10-minutes walk from Main Street. Head up the hill and turn left at Church Circle. But you can also catch a shuttle or pedicab.
Church Circle contains St. Anne’s Episcopal Church, founded in 1692 and famous for its two Tiffany windows.
The church is open to visitors daily, but walk in quietly as there may be people in reflection or prayer. Guided tours are offered on the first and Mondays of the month from 10am-11am and on Wednesdays from 12:30pm-2pm.
Across from the church is the oldest tavern in Annapolis, Reynolds Tavern and the 1747 Pub downstairs. This is also one of the oldest pubs in the U.S.
Reynolds Tavern serves a full lunch menu, English afternoon tea, and dinner. In the spring, summer and early fall, we offer casual, alfresco dining in the courtyard. The cellar pub in the Tavern’s original kitchen gives you a flavor of the Tavern’s rich history.
The first block of West Street is full of restaurants and bars, most having music on the weekends and several with music during the week year round.
You’ll find Rams Head, a well-maintained colonial bar/restaurant with a beautiful outside courtyard open in the summer. Rams Head On Stage offers national bands and comedy acts that swing by on their way between major venues.
Rams Head Tavern Annapolis, one of the town’s most popular Colonial bar, features house drafts from their brewery, Fordham and Dominion Brewing, located in Dover, Delaware. Rams Head On Stage, next to Rams Head Tavern, offers nightly music & comedy shows.
Stan & Joes is a well-loved dive-bar where the local sports teams hang out with corn hole and a crush stand in the open-air back patio area.
Across from Rams Head is the Annapolis visitor center. The West Street Visitors Center is open daily from 9:00 a.m. until 5:00 p.m., except on Thanksgiving, Christmas, and New Year’s Day.
Aside from the galleries, there’s not much shopping on West Street. But on the first Sunday of the month, from May through October, it becomes the site of the First Sunday Arts Festival. The street is closed and artisan booths line the curbs.
A number of restaurants continue for several more blocks.
A couple places to consider further down the street: The Metropolitan has a gorgeous rooftop bar with billowing curtains and cushioned lounging areas. It features alternative rock at night. Lemongrass is the most popular Asian restaurant of the area, specializing in Thai food.
Annapolis residents eat early, so the crowd thins past 7pm.
To locals, “West Street” section of town generally ends when you reach Westgate Circle, with three of Annapolis’ most well-known restaurants: Fado’s Irish Pub, Carpaccio’s Tuscan Kitchen and Miss Shirley’s Cafe.
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