Chestertown, Maryland is a picturesque, historic town on the Chesapeake Bay. Founded in 1706, Chestertown is full of old-world charm, beautiful views, and interesting places to explore with a date. With numerous parks, galleries, restaurants, and music venues, Chestertown offers something for everyone.
1. Chestertown parks and places for a walk on a first date
There are a number of great parks and places to take a walk in Chestertown. The historic Wilmer Park, located near the water, is a perfect place to take a romantic stroll. The park is full of lush trees, large grassy areas, and plenty of seating areas to sit and chat with your date. Another great option is the Stewart Park and Gardens, located on the Eastern Neck Island National Wildlife Refuge. Here you can enjoy the views of the bay and take a peaceful walk along the paths.
2. Places for a coffee date in Chestertown
For a casual coffee meet-up, Latte Da is the perfect spot. This cozy cafe offers a variety of hot and cold drinks, as well as delicious snacks. Make sure to check out the outdoor seating area with views of the Chester River. The River Arts Center is another great spot, with a cafe serving locally-sourced snacks and coffee. It’s a great place to browse local art and discuss culture over a cup of coffee.
3. Chestertown galleries, museums and exhibitions to visit on a date
If you’re interested in art and culture, there are plenty of galleries and museums to explore in Chestertown. The Tuckahoe Steam & Gas Show is a great place to learn about local history. The show features a collection of antique steam engines, tractors, and equipment from the 19th and 20th centuries. You can also visit the Historic Chestertown Visitor Center to learn about local history and explore the exhibits.
4. Live music and entertainment to invite your date to in Chestertown
For a truly unique date experience, check out the live music and entertainment venues in Chestertown. The Mainstay is a great spot to catch local and touring music acts. The bar also offers plenty of great beer and food, making it a great place to spend an evening with your date. The Eastern Shore Performing Arts Center is a great place to catch a show. From theatre performances to comedy acts, this venue has something for everyone.
5. Chestertown pubs, bars or restaurants for a first date drink or food
When it comes to drinks and food, Chestertown has plenty of pubs, bars, and restaurants to choose from. The Imperial is a great spot to grab drinks and indulge in some pub eats. The bar also features live music, making it the perfect place for a date night. The Bartlett Pear Inn is a great spot for dinner and drinks. The restaurant serves up classic American fare with a modern twist.
6. Other date ideas to try in Chestertown
If you're looking for something a little different, check out the other date ideas Chestertown has to offer. The Bigscreen Movie Theater offers a classic movie-going experience, with a variety of films to choose from. Or for a little more adventure, take your date on a sailing trip. Chestertown Water Tours offers a variety of boat tours, giving you the perfect opportunity to take in the beautiful views of the Chesapeake Bay.
