The 12 best things to do in MetroWest this weekend

September 25–27, 2026 · handpicked from everything on across MetroWest.

MetroWest's weekend leans heavily into live music — porch-hopping in Natick, jazz in a converted Newton club, and a fife-and-drum muster in Sudbury — while Applefest and an Oktoberfest-style bash bring the fall-festival energy, even with a few storm-related postponements on the calendar.

Natick Center PorchfestSaturday · 2:00 PM · Natick Center and surrounding locations · NatickA day-long wander through Natick Center as local bands play from porches and driveways across town — sponsored by Music Go Round Boston, with a full map of the action on the event page.Cherry Street Music Presents Jazz Legends Donna McElroy & George Russell Jr.Saturday · 7:00 PM · The Allen Center · NewtonThe Allen Center turns into a cozy, intimate jazz club for the night, with table seating, drinks, and bar snacks as Cherry Street Music brings in veteran vocalist Donna McElroy and George Russell Jr. for an evening of jazz.The Linda Ronstadt ExperienceSaturday · 8:00 PM · TCAN · NatickTCAN hosts a tribute act channeling Linda Ronstadt's catalog — a solid pick if you're in the mood for a night of classic rock and country hits without leaving Natick.Applefest Street FairSaturday · 10:00 AM · Blake Street · NorthboroughBlake Street fills with dozens of vendors for the Rotary Club of Northborough's annual Applefest Street Fair, the kind of classic New England fall street fair worth wandering through.Colonial Faire and Muster of Companies of Fyfes and DrumsSaturday · 10:00 AM · Longfellow's Wayside Inn · SudburyStep back to 1775 at Longfellow's Wayside Inn, where fyfe and drum companies muster alongside colonial-era demonstrations, contradancing, weaving, and blacksmithing — good for history buffs and kids alike."A"ktoberfest Rhythm & BrewsSunday · 11:00 AM · NARA Park · ActonNARA Park's fall festival pairs a full day of live music with a biergarten of local and seasonal brews, Bavarian-style food, and games — an easy way to ease into Oktoberfest season.Kris Adams TrioSaturday · 6:00 PM · HollistonThe Kris Adams Trio returns for an after-hours set on the main floor of Holliston Public Library — a relaxed, unexpected spot to catch some jazz on a Saturday evening.Choral & Chamber Music FestivalSaturday · 7:30 PM · Holy Trinity Armenian Church · BelmontHoly Trinity Armenian Church launches its inaugural two-day Choral & Chamber Music Festival, themed "Liberty Chimes" for the 250th anniversary of American independence, blending Armenian and American music traditions.Bat Boy: The MusicalSunday · 3:00 PM · Umbrella Arts · ConcordUmbrella Arts opens its run of the cult musical Bat Boy in Concord — a strange, funny, surprisingly heartfelt show for anyone craving something offbeat this Sunday.Hop/Up Wellness Weekend Sept. 25-27Friday · 12:00 AM · Hopkinton Independent – Events · HopkintonBlack Door Yoga's three-day wellness weekend raises funds for food banks at Project Just Because and the United Parish Church of Upton — a feel-good way to kick off the weekend in Hopkinton.Julio's Fall Bitters, Amaro & Beer FestSaturday · 2:00 PM · Julio's Liquors · WestboroughJulio's Liquors hosts an afternoon tasting built around craft beer, bitters, and amaro — a good detour for anyone curious about fall's more bittersweet flavors.LIVE FROM...BELMONT BOOKS! : Venus WindsSunday · 4:30 PM · Belmont Books · BelmontBelmont Books' monthly live-music series continues with Venus Winds, a wind quintet dedicated to spotlighting women in music, playing right in the bookstore on Sunday afternoon.

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