Zach Bryan rolls into Gillette Stadium
Milo’s Five · MetroWest · October 1–7, 2026
Stadium rock rubs shoulders with bluegrass and a harvest fair this week, plus a street closes for a day of vendors and cider. Pick your scale — arena roar or porch-light acoustic — and go.
Pick of the weekZach Bryan headlines Gillette with heavy supportZach Bryan plays Gillette Stadium with Gregory Alan Isakov and Gabriella Rose backing the bill — a stadium-scale rock/pop night.Friday · 7:00 PM · Gillette Stadium · Foxborough · Zach Bryan - With Heaven On TourGrammy-nominated bluegrass lands at TCANDella Mae, the Grammy-nominated bluegrass band, plays TCAN in Natick — a rare chance to catch a national act in a small room.Friday · 8:00 PM · TCAN · Natick · Della MaeBring the kidsAndrew Avenue turns into a street fairThe Wayland Festival shuts down Andrew Avenue for a full day, 10am to 5pm, turning the town center into a pedestrian zone.Saturday · 10:00 AM · Andrew Avenue, Wayland, MA, 01778 · Wayland · Wayland FestivalFall officially starts at Greene's FieldThe Needham Harvest Fair takes over Greene's Field Sunday from 11 to 3, the kind of low-key fall ritual worth building an afternoon around.Sunday · 11:00 AM · Greene's Field · Needham · Needham Harvest FairHip-hop and trap on a Tuesday nightStruggle Jennings brings hip-hop and trap to Six String Grill and Stage in Foxborough, a genre change of pace for a Tuesday.Tuesday · 7:00 PM · Six String Grill and Stage · Foxborough · Struggle Jennings
Also worth a line
- Ronnie Earl and The Broadcasters play TCAN Saturday, back to back with Della Mae's Friday show.
- Jack's Abby runs four days of German food and seasonal beers in Framingham, October 1 through 4.
- A McCartney tribute act that reportedly impressed George Martin himself hits the Regent Theatre.
- Julio's Liquors pours over 100 premium sakes for an afternoon tasting in Westborough.
- Bellforge Arts Center in Medfield hosts its annual celebration of the community's many cultures.
See you out there — Milo
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