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, plant sales, garden tours, and community celebrations, there’s something for everyone. 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 Events
May 23rd: Discovery Day, Lexington. Kick off Memorial Day weekend with Lexington’s town-wide street fair from 10am–3pm. Local businesses, restaurants, civic organizations, and community groups line Massachusetts Avenue in Lexington Center for a family-friendly day of food, shopping, giveaways, and fun.
May 28th: Bedford Prom Stroll, Bedford. Join Barrett Sotheby’s International Realty and the Bedford community in congratulating the Bedford High School graduating class as they head to prom! The event begins at 4pm at Bedford High School.
June Events
June 5th–6th: Concord Museum Garden Tour, Concord. Hosted by Concord Museum, this ticketed tour features six stunning private gardens throughout Concord. The tour runs from 10am–4pm, and proceeds support the Museum’s school programs.
June 6th: Winchester Town Day, Winchester. This annual community celebration brings vendor booths, local organizations, entertainment, food, family activities, and town-wide festivities to downtown Winchester. The day wraps up with fireworks at Manchester Field.
June 20th: Old Home Day, Carlisle. This free, family-friendly event features traditional favorites such as the Great Parade and the Country fair, alongside newer highlights like a parkour challenge and the weekend-long music festival.
June 20th: Urban Garden Tour, Melrose. Hosted as part of the Melrose Farmers’ Market special events calendar, this garden tour takes place from 10am–1pm and is a great pick for garden lovers looking for local inspiration.
June 20th: Strawberries ‘n Arts Festival, Westford. Held on Westford Town Common from 10am–3pm, this annual event features local artisans, food vendors, and plenty of strawberry-themed treats.
June 21st: Fifer’s Day, Boxborough. This family festival at Flerra Meadows starts with a road race, followed by a parade and other attractions, including food and drink, music, craft fair vendors, kids’ activities, 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!