Spring is in full swing and it's one of the best times to be in New England! During May and June, communities across the Patriot's Trail region come alive with a vibrant array of events. From parades and carnival rides to craft fairs and plant sales, there's something for everyone — all buzzing with the spirit of community support. Don’t miss out on the fun — check out our list of local events and join the festivities to fully embrace the springtime spirit!
May 24th: Discovery Day, Lexington. Kick off Memorial Day weekend with a street fair along Mass Ave! From 10am – 3pm, local businesses will have booths with giveaways and prizes, plus a beer garden courtesy of Craft Food Halls.
May 29th: Prom Stroll, Bedford. Join Barrett Sotheby’s International Realty in congratulating the Bedford High School graduating class of 2025 as they head to their prom!
June 6th- 7th: Concord Museum Annual Garden Tour, Concord. Hosted by Concord Museum, this ticketed tour features 6 stunning private gardens in Concord. All proceeds benefit the Museum’s school programs, serving K-12 programs across the Commonwealth.
June 7th: Winchester Town Day. Annual street fair with local businesses providing games, entertainment and shopping for visitors. Highlights include the Pancake Breakfast, WFEE Road Race and Fishing Derby in the morning, and the Dog Show and Beer Garden in the afternoon. The event rounds off with an evening fireworks display. Get a head start on festivities at the Friday Night Block Party featuring Matt Heaton!
June 21st: 57th Annual Fifer’s Day, Boxborough. This family festival at Flerra Meadows starts with a road race, followed by a parade and other attractions, including food & drink, bouncy castles, music, craft fair and a volleyball tournament.
If you want more ideas for things to do this spring, ask our agents! They live and work in these towns and would love to share their recommendations. And check back next month for our list of local outdoor music events this summer!