Top 12 Things To Do In Chesapeake City, Maryland

things to do in Chesapeake-City MD
Richard Dean
Richard Dean 
Updated
| 5 min read

Located on a working commercial canal, Chesapeake City is a gorgeous town in Maryland. Chesapeake has weather that brings everybody out for an adventure. This town has long been known for its magnificent sea-going vessels inland view, which serves as a reminder of its great history. Despite its not so good past (a disorganized town) because of the dispiriting depression era, Chesapeake City has now become a beautiful and progressive place with great hospitality. Seasonal events, outdoor activities, stunning stores, a splendid culinary scene, superb accommodation - these are just a fraction of the action that you can get at Chesapeake City. Check out this article and discover the best things to do in Chesapeake City, Maryland.

1. Discover the historic exhibits at C & D Canal Museum

Chesapeake City C&D Canal Museum - water lift pump house

Posted by David Hoatson on Monday, 8 July 2019

Located in the heart of Chesapeake City, Maryland, you will find a long-known gem - the C & D Canal House Museum. This 137.16 m (450 ft) wide and 22.53 km (14 mi) long canal of Chesapeake has plenty of stories to tell. The museum features exhibits, pictures, some actual equipment, interactive models (old canal locks), and more. And as you walk to the grounds, you’ll have the opportunity to see a big ship container go by. You will learn a lot here for free!

C & D Canal Museum

Address: 815 Bethel Rd, Chesapeake City, MD 21915, USA

Website: C & D Canal Museum

Opening hours: Mon - Fri: 7am - 3:30pm; Sat: 11am - 12am; Sun: 11am - 4pm

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2. Take a cruise with Chesapeake City Water Tours

Posted by Chesapeake City Water Tours on Saturday, 23 September 2017

Chesapeake City Water Tours provides wonderful getaways, from sightseeing tours to sunset cruises, from beer/wine tastings to booze cruises. This 15.24-m (50-ft) custom-built Catamaran can cater to up to 49 guests and it has plenty of entertainment facilities to keep you upbeat, like a full bar and sound system. The whole experience is worth every penny. Your journey gives you the opportunity for sightseeing and allows you to learn about the history of the canal in a comfortable and fun atmosphere. This is also a cool venue for a party.

Chesapeake City Water Tours

Address: 108 Bohemia Ave, Chesapeake City, MD 21915, USA

Website: Chesapeake City Water Tours

Opening hours: 9am - 8pm (daily)

Price: From 17 USD

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3. Taste beer varieties at Bayheads Brewing Company


Experience the taste of Chesapeake City’s first and only brewery: Bayheads Brewing Company. Founded by three local gentlemen who are passionate about craft beer, you can now choose to taste the beer in flights, pints, or growlers in a cozy and vibrant atmosphere, plus the food here is also good. In Bayhead, great beers are equal to good company.

Bayheads Brewing Company

Address: 2525 Augustine Herman Hwy D, Chesapeake City, MD 21915, USA

Website: Bayheads Brewing Company

Opening hours: Wed & Thu: 2pm - 9pm, Fri: 2pm - 10pm; Sat: 11am - 10pm, Sun: 12pm - 6pm (closed on Mon & Tue)

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4. Enjoy tasty cuisines at Chesapeake Inn Restaurant & Marina


Chesapeake Inn Restaurant & Marina is ready to serve you with their delicious food, impeccable service, and cozy atmosphere. Fresh tacos, salads, wood-burning brick oven pizzas, homemade burgers - everything on the menu promises a good dining experience. Entertainment is also the game here. There’s live entertainment on the deck and the tiki bar is also available. If you want more, they also serve mouthwatering sushi fresh from the ocean.

Chesapeake Inn Restaurant & Marina

Address: 605 2nd St, Chesapeake City, MD 21915, USA

Website: Chesapeake Inn Restaurant & Marina

Opening hours: Mon - Thu: 11am - 10pm; Fri: 11am - 11pm; Sat: 10am - 11pm; Sun: 10am - 10pm

Price: From 14 USD

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5. Book a tour with M/V Bay Breeze of Chesapeake City

Posted by M/V Bay Breeze of Chesapeake City on Saturday, 17 August 2019

M/V Bay Breeze of Chesapeake City must be included on your “special occasion list”. It is one of the top picks for boat tours and cruises along the beautiful Elk River and C&D Canal. It caters to special occasions, from a romantic date to an anniversary celebration to birthdays to a bachelorette party and even a charity and fundraising event. It is spacious enough and can hold up to 26 passengers. In every corner of the boat, amazing views are easy, plus the staff and captain are friendly and welcoming.

M/V Bay Breeze of Chesapeake City

Address: 208 Bank Street Chesapeake City, Maryland

Website: M/V Bay Breeze of Chesapeake City

Opening hours: Tue - Fri: 4pm - 6pm, 6:30pm - 8:30pm; Sat - Sun: 11am - 8:30pm (closed on Mon)

Price: 14 USD

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6. Indulge in coffee and sweets at Cafe on the Bay

It’s with much hesitation that I post this. Come on, it’s still August! I wasn’t ready! But people are asking..... we now have PUMPKIN SPICE! ?

Posted by Cafe On The Bay on Tuesday, 27 August 2019

Located in the heart of the beautiful Chesapeake City, you will find Cafe on the Bay. Cafe on the Bay is not limited to delicious hot coffee. They also offer a selection of sweet treats, desserts, pastries, lunch, and dinner. Start up your day with their bagel breakfast sandwich, which is best paired with Vanilla Honey Latte.

Cafe on the Bay

Address: 19 Bohemia Ave Chesapeake City, Maryland

Website: Cafe on the Bay

Opening hours: 6:45am - 5:30pm (daily)

Price: 6 USD

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7. Buy souvenirs at Belle on Bohemia


Little and cute treasures that will remind you of Chesapeake - if that’s what you are looking for, then visit Belle on Bohemia (formerly Belle Connell’s Emporium). This store is a combination of rustic charm, souvenirs, traveler’s items, and even homemade fudge and nostalgic candies. The ladies will twinkle with beautiful jewelry, and for the pet lovers and wine lovers, there is always something for them here. This place is in-demand for gift items and seasonal decorations, like Christmas decorations.

Belle on Bohemia

Address: 200 Bohemia Ave, Chesapeake City, MD 21915, USA

Website: Belle on Bohemia

Opening hours: Sun - Thu: 11am - 5pm; Fri: 11am - 6pm; Sat: 10am - 6pm

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8. Have some paintball fun at Outdoor Xtreme Chesapeake City

Posted by OXCC - Outdoor Xtreme Chesapeake City on Tuesday, 25 June 2019

In Outdoor Xtreme Chesapeake City, a blast is guaranteed. It features 65 acres (26.30 hectares) of Airsoft and Woodsball playing fields. It is equipped with almost everything suited for all kinds of outdoor activities, from Powerball to laser tag to paintball and more - all in quality and good condition. Meanwhile, splat master paintball is available for the kiddos.

Outdoor Xtreme Chesapeake City - Paintball & Airsoft

Address: 2941 Old Telegraph Rd, Chesapeake City, MD 21915, United States

Website: Outdoor Xtreme Chesapeake City - Paintball & Airsoft

Opening hours: Sat - Sun: 9am - 4pm (closed on Mon - Fri)

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9. Explore South Chesapeake City Historic District

Posted by Lazybones Outdoors on Wednesday, 19 April 2017

Whatever angle you look at it, South Chesapeake City Historic District is always charming. It serves as an important icon in Chesapeake City, which depicts the town’s glorious times (mid-19th century). Situated on National and Maryland Historic Registries, you will find gorgeous restored homes, Canal Museum, eateries, antique stores, and this spot is also a great venue for summer concerts.

South Chesapeake City Historic District

Address: Chesapeake City, MD 21915, United States

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10. Taste the finest wine at Chateau Bu-De, LLC Bohemia Manor Farm

Posted by Chateau Bu-De Winery, Bohemia Manor Farm on Monday, 11 February 2019

Chateau Bu-De, LLC Bohemia Manor Farm is a stunning 440-acre (178.06-hectare) farm, which is located in the historic property of Augustine Herrman (Bohemian explorer). If you want to experience the finest wines in Maryland, there’s no better place to go but here. Overall, this farm is a combination of a good atmosphere, nice people, delicious wines, and amazing views. If you’re lucky enough, live music and spectacular fireworks are also available.

Chateau Bu-De, LLC Bohemia Manor Farm

Address: 237 Bohemia Manor Farm Ln, Chesapeake City, MD, USA

Website: Chateau Bu-De, LLC Bohemia Manor Farm

Opening hours: Fri - Sun: 11am - 7:30pm; Wed - Thu: 2pm - 7:30pm (closed on Mon & Tue)

Price: 20 USD

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11. Check out the book collections at Chesapeake Central Library

Posted by Chesapeake Public Library on Wednesday, 21 August 2019

If you are a bookish traveler, perhaps, visiting the museum and library are included on your list. Luckily, Chesapeake Central Library has the most friendly staff to accommodate you. What’s more? They also have plenty of programs and classes like Nursery Rhyme Time, Toddler Storytime, Family Day Out Fall Tree Planting - actually, the calendar is packed with activities. If you want to have a great time while learning, this library is the coolest place to be.

Chesapeake Central Library

Address: 298 Cedar Rd, Chesapeake, VA 23322, United States

Website: Chesapeake Central Library

Opening hours: Mon - Thu: 10am - 8pm; Fri: 10am - 6pm; Sat: 10am - 5pm; Sun: 1pm - 5pm

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12. Bike along Maryland's Ben Cardin C&D Canal Recreational Trail


Explore the new waterfront trail in Maryland. Maryland’s Ben Cardin C&D Canal Recreational Trail is now completed and open for all. It is connected to Delaware’s Michael Castle Trail, which extends along Chesapeake and Delaware’s north bank (C&D Canal). The merging of these routes gives possibilities to explore the charming and historical town of Delaware City and Chesapeake City.

Maryland's Ben Cardin C&D Canal Recreational Trail

Address: Chesapeake City, MD 21915, United States

Website: Maryland’s Ben Cardin C&D Canal Recreational Trail

Opening hours: 9am - 5pm (daily)

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Explore Chesapeake City

C and D Canal Pumphouse Exterior
Source: Photo by Wikimedia Commons user Acroterion used under CC BY-SA 3.0

Fine dining, cruise, the finest wine, history, good weather; almost everything you are looking for in a great holiday is already at Chesapeake. Famous for its scenic views, this part of Maryland should never be missed if you are looking for a relaxing vacation. Discover why Chesapeake is the top pick for a holiday.

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Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Richard, a writer and traveler, is also passionate about biking. When not immersed in bike parts or computers, he can be found at the market, hunting for ingredients to fuel his love for...Read more

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