A guide to what to do and where to go!

Annapolis Night Life Guide: City After Dark

Annapolis night life

Table of Contents

Annapolis night life guide: Uncover the vibrant and diverse nightlife that Annapolis, Maryland, has to offer. From cozy bars and live music venues to late-night eateries and waterfront strolls, this city has something for everyone when the sun goes down.

Annapolis is a city which attracts tourists due to its maritime culture, rich history and beautiful scenic spots. But as the sun goes down and stars appear in the sky, Annapolis changes its colors and transforms into a center of nighttime entertainment. This blog will help you in navigating through the Annapolis night life guide, whether you are a local or a visitor.

Vibrant Bars and Pubs

Historic Downtown Pubs

Annapolis’ historic downtown area is home to some of the best pubs in Maryland.

Rams Head Tavern offers you a delightful mix of craft beers and live performances, making it a must-visit spot in your Annapolis Night life Guide. 

Reynolds Tavern is considered an historical landmark by many Annapolitans. The unique architecture and history compels the visitors to spend some quality time at this exciting venue.

Waterfront Bars

For those who enjoy scenic views with their cocktails, the waterfront bars provide an unforgettable experience. 

Pusser’s Caribbean Grille not only offers delicious tropical drinks but also stunning views of the harbor, perfect for a relaxing evening.

Live Music and Entertainment

Concert Venues

Annapolis boasts a vibrant music scene, with venues like Rams Head On Stage hosting both local and national acts. This intimate concert setting is renowned for its acoustics and ambiance, making it a cornerstone of Annapolis nightlife.

Local Talent and Open Mic Nights

49 West Coffeehouse provides a great way to discover new artists and enjoy a variety of musical styles.

Late-Night Dining

Gourmet Eateries

When it comes to food, Annapolis doesn’t disappoint. Late-night dining options like Iron Rooster serve up delicious comfort food well into the night. Their famous all-day breakfast menu is a hit among locals and visitors

Food Trucks and Street Food

If you’re on the go, Annapolis’ food truck scene offers a variety of late-night bites. From tacos to gourmet burgers, there’s something to satisfy every craving.

Cultural Experiences

Night Tours

If you are looking for an entertaining and spooky night tour, Annapolis Ghost Tours can offer you a memorable experience. These tours are best suited for people who are night owls.

Art Galleries and Night Markets

The First Sunday Arts Festival extends into the night during the summer months. Browse through local art, crafts, and enjoy live performances in a vibrant street market setting. Art enthusiasts can find this place a haven.

Outdoor Activities

Starlight Walks and Cruises

Enjoy a romantic evening stroll along the Annapolis waterfront or take a moonlight cruise on the Chesapeake Bay. These serene activities offer a perfect escape from the bustling nightlife while still enjoying the city’s beauty.

Sail Selina II can take you on a moonlight cruise away from the noise of the city and you can enjoy champagne over the waves.

sail selina moonlight cruise dining

Evening Picnics

City Dock is an ideal spot for an evening picnic. Pack a basket, bring a blanket, and enjoy the calm waters and beautiful night sky, making it a perfect end to your night in Annapolis.

city dock annapolis 
annapolis night life guide

Tips for a Great Night Out in Annapolis

  • Plan Ahead: Check event schedules and make reservations, especially on weekends.
  • Transportation: Utilize local taxis or rideshare services for a safe journey home.
  • Dress Code: Some venues have specific dress codes, so it’s good to know beforehand.


What are the best bars in Annapolis?

The best bars include Rams Head Tavern and Pusser’s Caribbean Grille, known for their unique drinks and lively atmosphere.

Are there live music venues in Annapolis?

Yes, Rams Head On Stage and 49 West Coffeehouse are popular spots for live music.

Can you find late-night dining in Annapolis?

Absolutely, places like Iron Rooster offer late-night dining options.

What cultural experiences are available at night in Annapolis?

Night tours and the First Sunday Arts Festival provide unique cultural experiences.

What outdoor activities can you do at night in Annapolis?

Enjoy starlit walks along the waterfront or take a moonlit cruise on the Chesapeake Bay.

Is transportation readily available at night in Annapolis?

Yes, local taxis and rideshare services are available for easy transportation.


Annapolis’ nightlife is as diverse and dynamic as its daytime attractions. Whether you’re looking for a quiet night by the water or a lively evening filled with music and entertainment, this Annapolis night life guide ensures you’ll have an unforgettable experience. Explore, enjoy, and embrace the charm of Annapolis after dark.


More to explorer

the picture of historic inns of Annapolis

Discover the Best Hotels in Annapolis, MD

Annapolis, Maryland, is a charming historic city that can captivate you in it’s waterfronts, vibrant culture, and rich history. Whether you’re visiting