Josh Ritter headlines TCAN's benefit night

This week leans festive — Medfield turns 375, Natick throws its biggest fundraiser of the year, and even the dogs get dressed up. Plenty to fill five days if you pace yourself.

TPick of the weekJosh Ritter headlines Natick's annual fundraiserTCAN's annual benefit brings guest artist Josh Ritter to the Natick stage for one night only.Saturday · 7:30 PM · TCAN · Natick · TCAN Annual Benefit 2026BDogs dress up, drink on, benefit rescueA costume contest, live music and patio drinks all benefit Last Hope K9 Rescue on Baramor's patio.Thursday · 5:30 PM · Baramor · 6th Annual Barktoberfest — Dog Costume Party & ContestMMBring the kidsMedfield throws itself a 375th birthday bashA parade and park celebration mark the town's 375th anniversary, with festivities running all day Saturday.Saturday · 9:00 AM · MEDFIELD, MASS · Medfield · Medfield 375th Anniversary Parade and CelebrationFCWorth the driveAward-winning bluegrass fills a Littleton churchThe Tenderbellies, an award-winning folk/bluegrass act, play one night only at First Church Unitarian in Littleton.Saturday · 7:00 PM · First Church Unitarian · Littleton · The Tenderbellies - LIVE award-winning folk/bluegrass!WMSleeperUkuleles take over the Waltham MuseumA Halloween-themed ukulele sing-along at the Waltham Museum, songbook included, all skill levels welcome.Monday · 7:00 PM · The Waltham Museum · Waltham · Watch City Ukers Boo-kulele at the Waltham Museum

Grab a jacket, the nights are getting good — Milo

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