Chestertown. You have probably never heard of it, but, this is my happy place. My moments of most peace have been sitting on a dock watching the sunset here. It is a quaint town on the Eastern shore, but boy does it have character. As the town motto describes it perfectly, “Historic colonial town on the Chester River”; this town was founded in 1706 and has endless entertainment opportunities.
This is not necessarily a destination on my bucket list, but currently, I long to be here on a beautiful day. When the weather is cold and I could rather be rocking on a boat on a warm day, it makes me miss it. With not a care in the world just sitting on the dock taking in everything around. The reason I am writing about this is to urge everyone to look into visiting here on their next family vacation and staying at Brampton Inn a very cozy bed and breakfast located right outside of town. I urge you to visit this town and just take in the quietness, there is no other way to describe it. This town is predominantly aged 60+ but has told me so many great lessons. When anyone our age visits this town they come out more mature as one is interacting with strictly adults which forces them slightly out of their comfort zone if they do not normally interact and socialize with the middle-aged community.
But, it is now time to get to the meat of Chestertown and many of the sights this town has to offer. The most well-known aspect of this town is Widehall which is from the 1760s. This house has become a gathering place for a majority of the town due to the huge yard and porches making this the ideal party house for the town’s Tea Party Weekend which brings in Marylanders from all towns. During this weekend, the town is busier than ever with parades and even a reenactment of the 1773 Boston Tea Party. Widehall is even featured on all of the yearly t-shirts due to its prominence in the town.
The Chestertown Marina is home to one of Maryland’s gems, the Sultana, which is a real-life replica of a British Royal Navy ship that is docked in Chestertown when it is not being used. This ship is used for Chestertown’s Tea Party weekend and is another predominant symbol in the town. I would recommend seeing this beautiful wooden ship as it is another core aspect of this area. This ship will sail and take Maryland students out on the water for school trips from Chestertown, Annapolis, Baltimore, St. Michaels, Cambridge, Oxford, Solomons, and Crisfield, all towns in the Chesapeake Bay area. For more information on Sultana, I would recommend looking at their website.
Chestertown is where I have felt the greatest peace. This town is located right on the water as previously mentioned, so I would allot a good chunk of time to just sitting, relaxing, and enjoying a view of the water as this provides an absolute reset and sit with the silence. When I am asked where my happy place is sitting along the water on the dock with family and friends around as well as some music playing. You have to do this. The whole world around you goes silent and nothing in the world can bother you. This is an absolute must- just watching the boats drive by-so start planning your trip to Chestertown.
In the finale of this condensed visit, you have to take a trip to Waterman’s a restaurant in the town over, Rock Hall. This restaurant is the dream. This restaurant is located right on Rock Hall Marina making this ideal for hungry boaters or those just looking to grab a bite. If given the opportunity, reserve here for around sunset and sit outside so you get the full experience of eating right on the water with the sun setting and a view of the Bay Bridge to Annapolis, Maryland. Since this trip will have to take place in the summer to get the full experience, one would have the benefit of the Maryland Blue crabs being in season. This is a rather obvious choice in your time, but the Crabby Burger from here is to die for. This is a loaded burger with pretty much anything you could want with a glob of fresh crab dip on top. This is making my mouth water just thinking about it.
But overall, Chestertown, Maryland is somewhere everyone needs to visit at one point or another. To live in this town you have to have a boat, it is sort of a rite of passage, but maybe if you’re nice I’ll offer you a ride! This is soon to be my full-time residence so I have begun to love this quaint little town.