Things to Do in Winchester, Massachusetts


1. Visit the Winchester Town Common


Located in the heart of Winchester, the Town Common is a beautiful park where you can enjoy a leisurely stroll, have a picnic, or simply relax and soak in the surroundings. The park is also home to various events and festivals throughout the year, so be sure to check the town's event calendar.



2. Explore the Middlesex Fells Reservation


The Middlesex Fells Reservation offers over 2,500 acres of natural beauty to explore. You can enjoy hiking, biking, fishing, or picnicking in this peaceful oasis located just a short drive from Winchester. Don't forget to bring your camera to capture the stunning views!



3. Shop and Dine in Winchester Center


Winchester Center is a charming area with a variety of shops, boutiques, and restaurants to explore. Whether you're looking for unique gifts, trendy clothing, or delicious food, you'll find it here. Be sure to take a leisurely stroll down the streets and soak in the small-town charm.



4. Tour the Sanborn House


The Sanborn House is a historic home in Winchester that offers guided tours showcasing the town's history and architecture. You'll learn about the Sanborn family, who once lived in the house, and get a glimpse into life in Winchester during the 19th century. It's a must-visit for history buffs!



5. Attend a Performance at the Winchester High School Performing Arts Center


The Winchester High School Performing Arts Center hosts a variety of performances throughout the year, including plays, musicals, concerts, and more. Check the schedule and catch a show to support the local arts scene and be entertained by talented performers.



6. Play a Round of Golf at the Winchester Country Club


Golf enthusiasts will love hitting the links at the Winchester Country Club. This private club offers a challenging course with beautiful views and well-maintained greens. Whether you're a seasoned golfer or a beginner, you'll enjoy a day on the course at this picturesque club.