Plan Your Trip to Winchester.

 A trip like no other!

Looking for a day trip to a quintessential New England town loaded with premier shopping and dining?  Look no further than Winchester!

Walking through Winchester’s town center, you will find restaurants and stores that offer everything from coffee, baked goods, to pub and tavern food to delicious Italian cuisine.  Spend the day shopping in Winchester’s stores to find unique clothing, gifts, books, toys and even something for the furry friend in your life.  Winchester’s stores and restaurants are independently and locally owned so you can feel good about shopping and dining local here!

Want to get outside and enjoy nature?  Enjoy Winchester’s wildlife and lake views for free. Discover all that a day trip to Winchester has to offer. A visit to Winchester will not disappoint.  A Small Town, Big Destination!

Welcome to Winchester – We’re glad you stopped by to plan your trip!

If you are interested in planning a trip to Winchester, this is the perfect place to start. You can browse the pages of this site to learn about Winchester’s rich history, browse our businesses and check out the events on our calendar.

We invite you to follow us on Facebook, Instagram, and Twitter for regular updates and information.

Visit Winchester MA is a proud partner with the Love My Local MA Campaign, which invites you to put your money where your heart is – right here in Massachusetts. Learn more at and explore all that Massachusetts has to offer at

Don’t forget to use the #mylocalMA hashtag on social media!

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Plan your next visit!

We'll send you ideas and suggestions to make your next trip incredible!


Are you are planning a visit to Winchester? We are happy to tell you that all of Winchester’s downtown attractions are within a 10- to 15-minute walk from any parking area.

“Wright-Locke Farm is a must-visit trip! It’s open to the public to visit the historic 1827 barn, feed the chickens, say hi to the goats, stroll in the trails, and much more.”

thebluebomberBoston, Massachusetts

Trip Directions

Winchester is located only eight miles from Boston proper. The town is accessible by train (2 stations, one currently undergoing renovations), by bus or by car. The town speed limit is 25 mph town wide unless stated otherwise.

Winchester is part of the Tri-Community Greenway and is reachable by bicycle.