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Best things to do in Winchester

Discover the city through the eyes of locals. Find the best things to do, places to eat, and get priceless advice from the people who live here.

Natural Feature
“This is a great place to go for short hikes and walks. Some trails lead to gorgeous views of the city!”
2local recommendations
Grocery or Supermarket
$$
3local recommendations
Natural Feature
“Great fishing -- pond is stocked by the MA Dept of Fish & Game. 2 mile loop around the pond is paved and very well-maintained. Dogs permitted on leash. ”
3local recommendations
Meal Takeaway
$$
2local recommendations
Bar
$$
“Nice pub with dining room that has large open windows that open onto the street on warm days.”
3local recommendations
Bookstore
1local recommendations
Art Gallery
1local recommendations
Café
$
“Locally owned Gem in the heart of the downtown Winchester Coffeehouse district. (it's surrounded by all the big national coffee chain franchises) Small place though so not so good for large groups.”
2local recommendations
Bar
“Excellent, gourmet American, fusion restaurant. Outstanding menu & cocktails. ”
2local recommendations
Bar
2local recommendations
Bakery
$
“Hands down, the BEST artisan bread you will EVER have!! Must try the Cranberry Pecan loaf. Super nice owners.”
1local recommendations
Meal Takeaway
2local recommendations
Food
“This working farm is open to the public and free. Bring fruit to feed the goats and chickens or pick your own raspberries. Fresh produce and honey are available at the farm stand. The farm abuts the Lexington reservation with miles of easy hiking trails.”
1local recommendations
Cafe
$$
1local recommendations
Bar
$$
2local recommendations