Keep scrolling to find the 2025 lineup of summer concerts with your perfect blend of live music and stunning locations throughout Massachusetts.

Castle Hill (Ipswich)
Thursdays, August  21 & 28

Make the most of summer with a Castle Hill Picnic Concert, featuring a different family-friendly band performing on Castle Hill’s Grand Allee overlooking Crane Beach.

• Studio Two – Beatles Tribute Band (8/21)
• Orville Giddings Band – Boogie Blues (8/28)

Fruitlands Museum (Harvard)
Thursdays, August 21 & 28

Bring your blankets, lawn chairs, dancing shoes, and bug spray to enjoy a night of music with panoramic views and a stunning sunset on select Wednesday and Thursday nights throughout the summer.

• The James Montgomery Band (8/21)
• Duppy Conquerors (8/28)

Governor Hutchinson’s Field (Milton)
Saturday, September 6

Celebrate the end of summer with a family-friendly jazz concert on beautiful Hutchinson’s Field. Enjoy beer, wine, snacks, field games, and great music from Fred Woodard Collecitve. Bring your friends, chairs & blankets, and a picnic, if you like!

• Jazz Concert at Hutch (9/6)

Rocky Woods (Medfield)
Sunday, August 31

Settle in on the lawn for a great afternoon of music in the beautiful surroundings of Rocky Woods.

• Rock the Woods! Outdoor Music Festival (8/31)

Scenic Songs (Multiple Locations)
Saturdays, September 13 & 27

Join us in scenic locations across the state with some of your favorite performing artists for a special, unplugged live music experience like no other.

• Mark Erelli and Dinty Child (9/13 at World’s End)
• A Hiking Concert with Erin McKeown (9/27 at Peaked Mountain)

Naumkeag (Stockbridge)
Monday, August 25

Join us for the perfect end to a Berkshires summer day, featuring live music from the genre-blending sounds of Cold Chocolate—a dynamic fusion of Americana, folk, and soulful grooves.

• Sunset Picnic at Naumkeag: End of Summer Celebration! (8/25)

Powisset Farm (Dover)
Thursday, August 21

Kick back and relax at Powisset Farm on a Thursday evening this summer.

• Thursday Summer Sunsets at Powisset Farm
  • August 21 with Ethan Robbins

Weir River Farm (Hingham)
Thursday, August 28

Live music, local food, craft brews, and the South Shore’s best views!

• Sunset Picnics at Weir River Farm
  • August 28 – Aldous Collins with Widowmaker Brewing, Wanderlust food truck, The Sausage Guy, and Smiles by the Mile Ice Cream

World’s End (Hingham)
Saturday, August 23

Celebrate this remarkable property at the end of the summer!

• Summer Send-Off at World’s End (8/23)