The 12 best things to do in MetroWest this weekend

October 16–18, 2026 · handpicked from everything on across MetroWest.

This weekend brings together community celebrations, live music across multiple venues, and seasonal festivities—from Medfield's 375th anniversary parade to farm festivals and award-winning folk performances.

Doubleshot AcousticFriday · 7:30 PM · SKYBOKX 109 · NatickDoubleshot Acoustic plays your favorite singalong tunes at SKYBOKX 109 on Friday night with no cover charge and free parking—a relaxed way to kick off the weekend.Native Drumming, Song & DanceFriday · 5:00 PM · Medfield Public Library · MedfieldEastern Medicine Singers perform Native Drumming, Song & Dance at Medfield Public Library on Friday evening, timed to coincide with sunset for a special cultural experience.Medfield 375th Anniversary Parade and CelebrationSaturday · 9:00 AM · MEDFIELD, MASS · MedfieldMedfield celebrates 375 years with a huge parade and Party in the Park on Saturday afternoon, featuring live music, food, and community gathering at Meetinghouse Pond.16th Annual Farm DaySaturday · 1:00 PM · Waltham Fields Community Farm · WalthamWaltham Fields Community Farm's 16th Annual Farm Day on Saturday afternoon celebrates locally grown food and sustainable agriculture with hands-on activities and community connection.The Tenderbellies - LIVE award-winning folk/bluegrass!Saturday · 7:00 PM · First Church Unitarian · LittletonThe Tenderbellies, an award-winning folk and bluegrass act, perform at First Church Unitarian in Littleton on Saturday evening—a standout musical event worth the trip.TCAN Annual Benefit 2026Saturday · 7:30 PM · TCAN · NatickTCAN's Annual Benefit on Saturday night features guest artist Josh Ritter in Natick, combining live music with community support.Fernando Brandão QuartetSunday · 3:00 PM · WaylandBrazilian jazz pianist Fernando Brandão Quartet performs at Arts Wayland's Berklee Faculty Jazz Series on Sunday afternoon, bringing vibrant musical energy to Wayland.The Concord Orchestra presents "Dancing in Disguise"Sunday · 2:30 PM · ConcordThe Concord Orchestra presents "Dancing in Disguise" on Sunday afternoon at 2:30pm, offering a polished classical performance in Concord's intimate setting.Live Music – Max SullivanSunday · 1:00 PM · HopkintonMax Sullivan brings live music to Hopkinton on Sunday afternoon from 1-3pm every other week—a low-key local favorite for relaxed weekend listening.Goodnow Library's Fall Concert Series with Lucas KamonSunday · 3:00 PM · SudburyLucas Kamon returns for an uplifting afternoon of classical piano at Goodnow Library in Sudbury on Sunday, featuring pieces from a variety of composers.Between The LinesSunday · 2:00 PM · Concord Youth Theatre · ConcordConcord Youth Theatre's Teen Company performs "Between the Lines," an empowering musical based on Jodi Picoult's novel, on Sunday evening—a local theater gem.Natick Art Association Open StudiosSunday · 11:00 AM · NatickNatick Art Association's Open Studios continue Sunday afternoon, giving you a chance to meet local artists and view live demonstrations across multiple locations in town.

Looking for the current weekend? See what’s on in MetroWest this weekend →