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Discover the most popular places to visit in Chestertown
Washington College
8.6/10 (87 reviews)
Founded in 1782, Washington College is the first college chartered in the sovereign United States. Explore its picturesque campus with historic architecture and Chester River waterfront views.
Chestertown Historic District
This preserved colonial port town showcases America's maritime heritage through 18th-century architecture. Stroll brick sidewalks along the Chester River or visit during the annual Tea Party Festival reenactments.
Garfield Center for the Arts at the Prince Theater
6.8/10 (5 reviews)
This historic 1928 theater offers an intimate setting for plays, music, and lectures in downtown Chestertown. Catch a performance during the Jazz Festival or Short Attention Span Theatre for a memorable evening.
River Arts Chestertown
7.4/10 (6 reviews)
Chestertown RiverArts celebrates creativity with monthly themed exhibits and workshops. Explore rotating galleries, meet local artists, and time your visit for the spring "Paint the Town" event or October's Studio Tour.
Wilmer Park
8.2/10 (13 reviews)
Nestled along the Chester River, Wilmer Park offers serene waterfront views and a modern playground for families. Bring a picnic to enjoy in the green spaces or time your visit for one of the community concerts.
Historical Society of Kent County Maryland
7.4/10 (6 reviews)
Step inside the Geddes-Piper House, home to Kent County's historical treasures and curated exhibits. Explore Maryland's rich past through intimate galleries and knowledgeable guides who bring local stories to life.
Kings Town Park
Kings Town Park offers serene pathways winding through lush greenery in Chestertown, Maryland. Enjoy morning strolls or invigorating runs along the scenic trails away from urban bustle.
Crumpton Auction
8.8/10 (3 reviews)
Dixon's Auction at Crumpton showcases thousands of antiques, collectibles, and furniture in weekly discovery auctions. Arrive early to preview treasures and secure a bidder number before the fast-paced action begins.
"Clean and comfortable. My only complaint is I'm an early riser and coffee wasn't available till 7:00 but there is a dunkin' donuts across the street. I would stay again."
"The room seemed very old, but OK generally. It looked out on a very unattractive storage area. Staff leaves at 4:30 and I got there a little later so the woman had to go back inside and get my information (which she said was already on my room door though I didn't see that). This is an old hotel for the golf course and marina. Everything seems a little run down."
"Terrible !!! Dirty not clean the owner was rude and didn’t care about the conditions of the room. I asked for partial refund and was denied. Rat poop in the heaters. Dog hair in tubs dead bugs. Body fluids everywhere! Also drug dealers outside with guns. The owner still didn’t care what they were doing. Don’t go to this place it should be shut down !"
"Beautiful property! We did not take full advantage of Breakfast, simply because we came to relax and sleep in, and thank GOD, coffee was provided in our cottage. We did, however, catch the tail end of Breakfast one day, and it was fine. We had good conversation with the owners, two other guests, and another couple. We enjoyed the warm reception from the dogs, and found the complementary cookies and beverages generously stocked inside the Inn a surprisingly delicious amenity. Would suggest a...
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.