Skip to content

Best things to do in Winchester

Discover the city according to 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!”
2 locals recommend
Grocery or Supermarket
$$
3 locals recommend
Natural Feature
“Great fishing -- pond is stocked by the MA Dept of Fish & Game. 2 mile loop around the pond is paved and very well-maintained. Dogs permitted on leash. ”
3 locals recommend
Meal Takeaway
$$
2 locals recommend
Bookstore
1 local recommends
Bar
$$
“Nice pub with dining room that has large open windows that open onto the street on warm days.”
3 locals recommend
Art Gallery
1 local recommends
Café
$
“Locally owned Gem in the heart of the downtown Winchester Coffeehouse district. (it's surrounded by all the big national coffee chain franchises) Small place though so not so good for large groups.”
2 locals recommend
Bakery
$
“Hands down, the BEST artisan bread you will EVER have!! Must try the Cranberry Pecan loaf. Super nice owners.”
1 local recommends
Bar
“Excellent, gourmet American, fusion restaurant. Outstanding menu & cocktails. ”
2 locals recommend
Bar
2 locals recommend
Meal Takeaway
2 locals recommend
Cafe
$$
1 local recommends
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.”
1 local recommends
Bar
$$
2 locals recommend