Discover what happened and what’s next with our curated calendar of exclusive events and meaningful activities, both within our team and across the vibrant communities of Winchester and Greater Boston. This section keeps you connected to what matters most: elevated experiences, inspiring people, and the pulse of our region.

WINCHESTER FARMERS MARKET

Every Saturday in September (Sept 6, 13, 20, 27), the Winchester Farmers Market brings the Town Common to life from 9:30 AM to 1:30 PM. The market is more than just a place to shop — it’s a vibrant community gathering spot where neighbors connect over fresh, locally grown produce, baked goods, specialty foods, and handmade crafts.

Each weekend in September features live music, children’s activities, and rotating local vendors that celebrate the season’s harvest. With fall produce coming into full swing, visitors can expect apples, squash, greens, and artisanal foods alongside unique small-batch products. Community organizations and sustainability groups often set up informational tables, making the market both a lively shopping experience and a hub of local engagement.

The setting on Winchester Town Common provides a relaxed, family-friendly atmosphere — perfect for strolling, sampling, and supporting local farms and small businesses as summer fades into autumn.

Learn more at the official site: Winchester Farmers Market

MUSICFEST OPEN HOUSE

Discover your next instrument (or your child’s!) at Winchester Community Music School’s annual MusicFest Open House. For two lively hours, the whole building opens up for a school-wide instrument petting zoo, live demos, mini meet-the-instrument sessions, and a playful scavenger hunt with prizes. WCMS faculty and students are stationed throughout the rooms to help you try everything—from a tiny starter violin to a booming timpani—while answering questions about lessons, ensembles, and classes for kids, teens, and adults. It’s free, drop-in friendly, and perfect for curious beginners and music lovers alike.

• Winchester Community Music School, 407 Highland Ave, Winchester
• Sun, Sept 7, 2025 • 2:00–4:00 PM
• Free • All ages welcome

More details & RSVP: MusicFest Open House (WCMS)

GLEN DOHERTY MEMORIAL ROAD RACE

Honor a hometown hero and power a purpose at the 13th Annual Glen Doherty Memorial 5K/10K. Starting at 12:00 PM in front of Winchester Town Hall (71 Mt. Vernon St.), runners, walkers, ruckers, teams, and supporters take the streets for a spirited loop through town that celebrates Glen’s life and fuels the Glen Doherty Memorial Foundation’s scholarship programs for members of the Special Operations community transitioning to civilian careers. Expect an upbeat start-line ceremony, big community energy, and a course that’s friendly to all paces—whether you’re racing the 10K, cruising the 5K, or joining with friends as a team or in the ruck division. After you cross the finish, stick around the Town Common to cheer others in and enjoy the camaraderie that makes this day a Winchester favorite.

• Start/Finish: Winchester Town Hall
• Time: Sunday, Sept 21, 2025 • 12:00 PM
• Distances/Divisions: 5K & 10K, with Team and Ruck options
• Why it matters: Proceeds support GDMF scholars and Glen’s legacy of service

Details & registration: Glen Doherty Memorial Foundation — Road Race

YAPPY HOUR

Bring your pup and join us for Yappy Hour—a tail-wagging, community‑friendly gathering at Lord Hobo Brewing. This dog-friendly mini‑festival happens one Sunday each month through the summer, wrapping up the series on September 21. Expect chilly craft beers for the humans and plenty of treats for the four‑legged guests. It’s an easygoing, open‑air hangout where pups can mingle while their humans enjoy great brews and laid‑back conversation. Ideal for Winchester dog owners looking for a fun weekend outing with friends and furry companions.

What You’ll Find:

• A casual outdoor setting at Lord Hobo’s Woburn brewery
• Cold, locally brewed beers on tap for the adults
• Doggy treats and friendly sniffs for pups
• A community vibe—you and your pup name get noticed and make new friends
• A perfect way to cap off the summer dog-social season!