Top 6 nightlife & evening things to do in Annapolis

1. Private cultural walking tour of historic Annapolis

Two hours of flat walking — explore historic Annapolis waterfront with a focus on culture and storytelling from local history.

2. Historical pub crawl in Annapolis

Two-hour walking tour through downtown Annapolis — explore historical tales paired with drinks at each location, offering insights into the city’s past.

“I strongly recommend this tour! It was enjoyable and informative, and I really appreciated the choice of bars and drink recommendations. I had a fantastic time.”— TracySeiger

3. Historic pub crawl in Annapolis: tales of scandal and intrigue

Two hours of bar-hopping (approx. 0.5 miles) — visit three local taverns while hearing stories of Annapolis' scandalous past and colorful history, adults only.

“Baltimore Tours and Crawls originated in Annapolis, so their expertise is evident. They provide a variety of engaging tours in the Fells Point area, including the Walking Ghost Tour, Haunted Pub Crawl, Twisted History Tour, Bootleggers & Rum Runners Tour, and the Sports Legends Tour. Each tour caters to different interests—historical, supernatural, athletic, and quirky stories. Departing from the historic Admiral Fells Inn around 8 PM, these tours last about 90 minutes. The Pub Crawl is particularly enjoyable if you’re not driving. The guides are highly knowledgeable and entertaining, having earned the title of "Best Downtown Tour" in Fells Point for three consecutive years. Dogs are welcome as long as they are leashed and friendly.”— Steve C

4. Haunted pub crawl in Historic Downtown Annapolis

Two hours touring the oldest haunted pubs with a guide, featuring ghost stories and a drink at each stop.

“Learning about the history of Annapolis while listening to ghost stories was a fantastic experience. Megan did an outstanding job as our tour guide.”— Daniel_H

5. Annapolis Ghost Tour and Haunted Pub Crawl

Two hours in Annapolis' historic district, sharing ghost stories while visiting local pubs. Drinks not included.

“I was skeptical about a haunted pub crawl on a Monday night, but it exceeded my expectations. Our small group felt intimate, almost like a private tour. Kat, our guide, was charming, well-informed, and an excellent storyteller. It provided a fantastic chance to learn about Annapolis while discovering some of its ghostly residents.”— KimHoffman13

6. Annapolis ghost tour — a walking exploration of haunted sites

A mile-long walking tour through Annapolis’ historic district, highlighting ghost stories and haunted buildings like the Middleton Tavern and James Brice House.

“Kat was entertaining and engaging! The ghost stories were fantastic, making for wonderful memories during my friend's 40th birthday getaway. The group size was just right, not too large at all.”— Diane_F