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Things to do in Cheshire County

Top recommendations from locals

From sightseeing to hidden gems, find out what makes the city unique with the help of the locals who know it best.
Scenic Viewpoint
“Very popular hiking mountain. Year around. Lots of trails. Be prepared. Research: Monadnock Mountain State Park .”
  • 50 locals recommend
Brewery
$$
“Right by the Connecticut River, amazing roof terrace. Look for the bald eagles.”
  • 62 locals recommend
Bar
“Harlow's is a local bar with great character, known for their great food and beer selection. They don't serve liquor (just wine and beer) but they have live, local music almost every night of the week. ”
  • 25 locals recommend
Theatre
“Award-winning local theater. The players are so very talented, and sure to entertain. ”
  • 20 locals recommend
Museum
“Ever-changing art exhibits and events in beautiful, historic train station, right in downtown Brattleboro.”
  • 26 locals recommend
Art Gallery
“Wonderful collection of artisan's work from around the world. Small gift shop of unique gifts. ”
  • 9 locals recommend
Bar
$$
“If you like oysters, or any sort of seafood, or even some fantastic Asian fusion cuisine, check out Pearl Restaurant and Oyster Bar. The owner/chef creates a menu of flavorful dishes that are perfectly seasoned and well-balanced. This place has quickly become my local favorite. ”
  • 13 locals recommend
Cinema
“The Colonial Theatre is an historic performing arts center, which brings the cultural and creative spirit of our community to life. Presenting Live Events and Fine Film”
  • 12 locals recommend
American Restaurant
$$$
“Fine dining, and a fun bar out front. Views of the river from the dining room and they have a private room for medium sized groups.”
  • 8 locals recommend
Grocery or Supermarket
“Nearby groceries, eat-in deli, local treats, cheeses, and great wine, beer and cider selections. ”
  • 20 locals recommend
Indie Cinema
“The oldest still in operation movie theater in NH! It is a quaint, small town experience. ”
  • 7 locals recommend
Grocery or Supermarket
“Natural food grocery store and cafe, with an emphasis on local and organic foods.”
  • 10 locals recommend
American Restaurant
$$
“Delicious farm to table restaurant; ever-changing menu featuring local, fresh ingredients; cozy, friendly atmosphere in historic building; amazing weekend brunch with best coffee you've ever had!”
  • 18 locals recommend
Café
“Worth a visit to Walpole, NH for the chocolates, hot chocolate, and Sunday brunch. ”
  • 19 locals recommend
Café
$
“Aesop's Tables makes Devin's favorite breakfast; their breakfast sliders, with homemade English muffins! Their coffee is great as well and since it is located inside of the Toadstool Bookshop, you can shop while you wait for your food. ”
  • 7 locals recommend
Bookshop
“Wonderful store with thousands and thousands of titles in stock to browse and buy new and used books.”
  • 9 locals recommend

Top restaurants

Brewery
“Right by the Connecticut River, amazing roof terrace. Look for the bald eagles.”
  • 62 locals recommend
Bar
“Harlow's is a local bar with great character, known for their great food and beer selection. They don't serve liquor (just wine and beer) but they have live, local music almost every night of the week. ”
  • 25 locals recommend
Bar
“If you like oysters, or any sort of seafood, or even some fantastic Asian fusion cuisine, check out Pearl Restaurant and Oyster Bar. The owner/chef creates a menu of flavorful dishes that are perfectly seasoned and well-balanced. This place has quickly become my local favorite. ”
  • 13 locals recommend
American Restaurant
“Fine dining, and a fun bar out front. Views of the river from the dining room and they have a private room for medium sized groups.”
  • 8 locals recommend
American Restaurant
“Delicious farm to table restaurant; ever-changing menu featuring local, fresh ingredients; cozy, friendly atmosphere in historic building; amazing weekend brunch with best coffee you've ever had!”
  • 18 locals recommend
Café
“Aesop's Tables makes Devin's favorite breakfast; their breakfast sliders, with homemade English muffins! Their coffee is great as well and since it is located inside of the Toadstool Bookshop, you can shop while you wait for your food. ”
  • 7 locals recommend
Restaurant
“A great stop for Whiskey lovers, and all natural food served from within a 50 mile radius of Peterborough, NH.”
  • 7 locals recommend
Italian Restaurant
“Absolutely outstanding food. No other way to say it. Better make a reservation on Friday and Saturday! Perfect for intimate dinners or large family gatherings. (In town: 8-10 minutes walk from house!)”
  • 17 locals recommend

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