Top 10 Tips for Getting Settled in Winchester
1. Meet your neighbors
2. Check out the Town Calendar
3. Subscribe to our local paper, The Winchester Star
4. Get rid of your trash
5. Find the local markets
6. Start a new family tradition: raspberry picking
7. Get outside and play
8. Explore local arts
9. Brush up on your Winchester town history
10. Reading Resources
Meet your neighbors
Join the Winchester Neighbors Club. We hold regular coffee meetups for newcomers, cocktail parties, host playgroups, book group, ladies’ and guys’ night out events, and more. Learn more about other organizations in Winchester here
Check out the Town Calendar, WinCentral.org
Find discussions, town calendar and classifieds at Winchester’s web portal, WinCentral.org
Subscribe to the Winchester Star
Subscribe to our town newspaper, The Winchester Star. Annual cost of home delivery is $50. To subscribe, call 1-888-MY-PAPER.
Get rid of your trash
Where does my trash go? A surpise to many newcomers to Winchester, the town does not provide municipal trash pickup. You have two options: either bring it to the transfer station (the dump) yourself, or hire a private company to pick it up. Learn more about obtaining transfer station permits from the town, or see this list of private companies to pick up your trash (many also offer snow removal services).
Find the local markets
The Winchester Farmer’s Market is held every Saturday from the second Saturday in June through the end of October, 9:30 am to 1:30 pm on the Winchester Town Common.
Whole Foods is the nearest organic supermarket, 400 Cambridge Rd. in Woburn.
Super Stop & Shop is the nearest conventional supermarket, located at 695 Main St.
Start a new family tradition: Raspberry Picking
Pick your own raspberries at the Wright-Locke Farm at the end of summer. Learn more about the farm at the Wright-Locke Farm Conservancy website. Watch for the announcement of the beginning of picking season on the Winchester Town website, or by driving by to see if the the “open” sign is hung (78 Ridge Street).
Get outside and play
Enjoy the great outdoors! Winchester not only borders the expansive Middlesex Fells Reservation, but also has many smaller woodland hikes and trails. Check out the Winchester Woodlands Guide to explore natural areas of Winchester. Find a listing of playgrounds in town here. While you’re at it, learn more about the WNC-sponsored effort to revitalize the playground at Ginn Field: BeGinn Again.
Explore local arts
Winchester has lots of visual, theatre, and performance arts. The Next Door Theatre hosts ongoing musical and theatrical productions. The Winchester Community Music School holds musical performances free and open to the public, as well as monthly Open Mic nights. Art in August is a month-long art exhibition, with art being displayed in the windows of local businesses, art walks and “meet the artist” receptions ongoing throughout the month. The Winchester Cultural Council is the town’s committee for arts and culture.
Brush up on your Winchester town history
Learn about Winchester’s history: start with an overview here. Did you know our town was named after a man who never even set foot here? Read the sad tale here. Learn more about the Sanborn House Historical and Cultural Center and the Winchester Historical Society.
Reading Resources
Get reading - get your library card at the Winchester Public Library. It’s a great place to relax and do work, with free wifi. You can also request books online, learn about library events. Bookends is a local bookstore located in the heart of Winchester center that also serves as a community hub. Their windows are always full of flyers for community events, they host author signings, kids’ storytime and craft events. They offer free home delivery!


