Hidden History Pub Crawl of Historic Annapolis

Discover Annapolis’ Secret Past on a Historic Pub Crawl

The Hidden History Pub Crawl of Historic Annapolis offers a unique way to experience this charming city’s lesser-known tales. Priced at $30 per person and lasting around 2 hours, this tour departs from The Maryland Inn at 8:00 pm. It features visits to three historic taverns, where you can enjoy drink specials and hear stories about which tavern was the most popular brothel and which founding father was chased out. This tour is perfect for those interested in local lore beyond the usual sightseeing.

What sets this experience apart is its focus on lesser-known aspects of Annapolis history combined with the lively atmosphere of historic taverns. The tour is suitable for adults 21 and over, with a smart casual dress code. While drinks are not included, participants have ample time at each stop to purchase beverages. The tour’s engaging guides bring local tips for further exploration, making it a fun and informative evening.

Key Points

• Price and Duration: $30, approximately 2 hours long
• Visit Three Historic Taverns: including Middleton Tavern, Rams Head Tavern, and Federal House Bar & Grille
• Lesser-Known Stories: about Annapolis’ hidden past and famous taverns’ secrets
• Drink Specials: most bars offer special deals for participants
• Guided Experience: led by a local guide sharing intriguing tales
• Weather-Resilient: operates rain or shine, with optional disposable ponchos

Starting Point at The Maryland Inn in the Historic District

The tour kicks off at The Maryland Inn, located at 16 Church Cir, a central spot in Annapolis’ Historic District. From there, the guide takes the group on a spirited journey through three carefully selected taverns. The approximate 30-minute stay at each stop allows plenty of time to purchase beverages and listen to engaging stories about each venue’s lesser-known history.

The starting location is an ideal gateway into Annapolis, setting the tone for an evening filled with local lore and historic charm. The tour concludes at the Annapolis City Dock, situated at Dock St, giving participants easy access to explore more of the waterfront afterward.

Exploring the Historic Tavern Stops

Middleton Tavern is a popular spot with a historic reputation. The guide shares stories related to its past, including details about its reputation as a venue for nightlife and clandestine activities in earlier centuries. This tavern’s long-standing presence makes it a natural starting point for uncovering Annapolis’ hidden past.

Rams Head Tavern is another key stop, known for its lively atmosphere and local drink specials. The stories here often include fascinating anecdotes about its role in the city’s social scene, as well as some lesser-known historical facts.

Federal House Bar & Grille offers a blend of history and comfort, with a story that ties into Annapolis’ early days as a port city. The guide discusses the tavern’s notorious reputation and its connections to famous locals.

Other potential stops include Annapolis Market House, O’Briens Tavern, and Dock Street Bar & Grill, each contributing their own piece of the city’s storytelling mosaic. The exact sequence of stops may vary, but each venue provides a rich backdrop for tales about Annapolis’ past.

The Stories Behind the Tavern Walls

Throughout the crawl, the guide shares lesser-known stories about each tavern’s history, including tales of famous figures, secrets, and scandals. For instance, stories reveal which tavern was the most popular brothel in the city’s history, and which founding father was chased out of a tavern. These anecdotes offer a fascinating glimpse into Annapolis’ colorful past that many visitors may not encounter on standard tours.

The storytelling style combines historical facts with lively narration, helping guests connect with the city’s past in a relaxed, informal setting. The local tips provided at the end of the tour also help guests plan future explorations of Annapolis’ historic sites and hidden corners.

Practical Details and Group Size

This tour operates with a maximum of 25 travelers, ensuring a comfortable and engaging experience. The meeting point at The Maryland Inn is easy to find, and the tour runs rain or shine—just bring appropriate clothing or a disposable poncho, which can be purchased for $1 if needed.

Participants should have a moderate physical fitness level, as the tour involves walking between stops within the historic district. The smart casual dress code suits the relaxed yet refined ambiance of the taverns.

Value and What’s Included

For $30, guests receive a guided tour with a knowledgeable local guide. While alcoholic drinks are available for purchase, they are not included in the price. The focus remains on storytelling, local tips, and the historic ambiance of each venue.

The tour’s free cancellation policy provides flexibility, allowing cancellations up to 24 hours in advance for a full refund. This makes it a low-risk choice for those interested in exploring Annapolis’ hidden history in a fun and relaxed setting.

Why This Tour Stands Out from Other Annapolis Tours

Unlike more conventional sightseeing options, this pub crawl combines history and entertainment in a casual bar-hopping experience. It’s ideal for those who enjoy local stories, historic taverns, and a lively atmosphere. The tour’s focus on lesser-known tales helps differentiate it from typical historical walks, offering a refreshing take on Annapolis’ past.

The guided storytelling ensures that even casual drinkers learn something new about the city, and the drink specials add a value bonus. While it may appeal more to adults 21+, the 2-hour duration makes it a manageable and engaging evening activity.

Final Thoughts on the Hidden History Pub Crawl

This tour provides an entertaining, small-group look into Annapolis’ secret stories behind its historic taverns. The $30 price point combined with local guide insights and the chance to enjoy drink specials makes it a great value for those interested in local lore and hidden corners of the city.

Those seeking a relaxed, social experience with a touch of history will find this pub crawl delightful. It offers a unique perspective on Annapolis that complements more traditional sightseeing, ideal for visitors wanting an evening of storytelling and fun.

Frequently Asked Questions

Is this tour suitable for all ages?
No, the tour is limited to adults 21 and over due to the availability of alcoholic drinks and the pub environment.

Do I need to purchase drinks during the tour?
Drinks are not included in the price, but most taverns offer drink specials. Guests can purchase beverages at each stop.

What should I wear?
A smart casual outfit is recommended. Since the tour operates rain or shine, bring appropriate clothing or a disposable poncho if rain is expected.

Can I cancel or reschedule the tour?
Yes, free cancellation is available up to 24 hours in advance. Cancellations within that window are non-refundable.

Where does the tour end?
The tour concludes at Annapolis City Dock at Dock St, near the waterfront, making it easy to continue exploring afterward.