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Chestertown

Things to Do in Chestertown in 2025 - Top Attractions, Local Food, Hotels & Travel Tips (Updated June 2025) | Trip.com

About Chestertown

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Things to do in Chestertown

What to Do

Looking for things to do in Chestertown? We provide up-to-date info on everything from must-see scenic spots to local hangouts.

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Where to Stay

Discover the most popular places to stay in Chestertown, complete with recommendations from fellow travelers and special hotel offers

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What to Eat

Want to eat like a local? Don't miss out on these top Chestertown dishes and foodie spots.

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Popular Types of Attractions in Chestertown

Popular Attractions in Chestertown

Adirondack Adventures | Rustic Charm | Dynamite Hill Recreation Area

Popular Ranked Lists

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Popular Restaurants in Chestertown

Cafe Adirondack | Buttino's Italian Bistro | Black Bear | Loon Lake Market & Deli | The Place | O P Frederick's | Odd Duck | Angie's Restaurant | Bombers Place | Mobil Pizza | Main Street Ice Cream Parlor

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More Things To Do in Chestertown

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