Autumn is one of the best times to enjoy life in our local communities. From lively town days and arts festivals to music, food, and family-friendly activities, there are plenty of ways to celebrate the season close to home. These events not only bring neighbors together but also showcase the unique character of each town. With something for every age and interest, there’s no better excuse to get out and explore. Here’s a look at some of the upcoming events in Concord, Acton, Lexington, Bedford, Winchester, Belmont, and nearby towns.
Harvard Lions Club Fall Fest & 5K – Saturday, September 13, 2025
Kick off the afternoon with a 5K fun run, then enjoy live music, food, a beer garden, and kids’ games on the Harvard Library lawn. Free to attend, with proceeds supporting local charities and community programs.
Belmont Town Day – Sunday, September 14, 2025
Hosted by the Belmont Center Business Association, Town Day is a fun-filled afternoon of music, local vendors, and family activities. Enjoy kids’ rides, face painting, a classic car show, and special shopping and dining offers throughout Belmont Center. A great way to celebrate community and kick off the fall season.
Winchester Spirit Weekend – September 19–21, 2025
Organized with the Glen Doherty Memorial Foundation, Spirit Weekend honors Winchester’s hometown hero while celebrating the town’s vibrant community spirit. Festivities include downtown street events with live music, tours, Farmers' Market fun, a beer garden, and the Glen Doherty Memorial Race. A full weekend of shopping, dining, and community pride.
Bedford Town Day – Saturday, September 20, 2025
The day begins with the Bedford Day 5K at 8:30 a.m., raising funds for the Recreation Department Scholarship Fund. The parade follows at 10:30 a.m., leading into the Town Fair from 10 a.m.–2 p.m. with booths, food, and activities for all ages. Evening fireworks at 7:30 p.m. cap off this much-loved community tradition. Stop by our office to say hi to the Barrett Sotheby's International Realty team!
Lexington Fine Arts & Crafts Fair – Saturday, September 20, 2025
Now in its 32nd year, this juried arts festival showcases handmade works from regional artisans on the Visitors Center lawn. Browse pottery, jewelry, woodwork, photography, and more in a festive outdoor setting. Free to attend and a perfect place to find unique fall treasures while supporting local artists.
Acton Oktoberfest – Saturday, September 27, 2025
Held at Gardner Field in West Acton, Oktoberfest offers something for everyone: a lively beer garden, food court, vendor booths, raffles, and kids’ games like inflatables and crafts. Sponsored by local businesses, this free event draws neighbors together for a day of fun, music, and community spirit. The Barett Sotheby's International Realty team will be there with fun games and giveaways! Rain date is October 4.
Lexington Porchfest – Saturday, September 27, 2025
This free, volunteer-driven music festival transforms Lexington into a stage, with musicians performing on porches across town. Stroll from house to house enjoying local talent, and wrap up the day with a community sing-along. A lively and family-friendly way to experience Lexington’s creative spirit.
Discover West Concord Day – Saturday, October 18, 2025
Celebrate all things West Concord with live music, pumpkin decorating, raffles, food vendors, and activities for kids and families. Local shops and businesses join in with specials and open houses, making it a fun way to explore the neighborhood and connect with the community. Free and open to all.
Lincoln Scarecrow Classic 5K – Sunday, October 19, 2025
A scenic run or walk through Lincoln’s picturesque roads and trails, this race is lined with festive scarecrows and colorful fall foliage. Proceeds benefit the Lincoln Land Conservation Trust, making it both a fun and meaningful event. Families, walkers, and runners of all levels are welcome - make sure you stop by the Barrett Sotheby's International Realty table for some goodies!
No matter which event you choose, these fall festivals are a great way to support local businesses, enjoy time with friends and neighbors, and make the most of the season. Mark your calendar, invite a friend, and get ready to experience the best of our communities this autumn. And if you’d like to learn more about living in these towns, reach out to one of our local real estate advisors — we’d be happy to help.