Here is a Masslive Article on Summer Concert Series, both paid and free community events.
Many cities put on free or very cheap outdoor concerts during the summer. Here's the schedule for every single outdoor concert series I could find, grouped by county. I could not find any free concert series in the Berkshires.
All events are free unless otherwise marked.
Greenfield Energy Park Coop Concerts Summer Concert Series - Greenfield
6 to 8 p.m.
Katie Clarke and Larry LeBlanc, R & D, and Small Change, May 28th;
Pat & Tex LaMountain, Boys of the Landfill, and Orlen, Gabriel and Avery, June 4:
Jim Eagan, and Joe Graveline, Nina Gross, and Dust Devils, June 11;
133 Skeele, Hope Street, and Little Wild Bouquet, June 18;
R & D and Psychedelic Farm Girls, June 25;
Jennie McAvoy, 133 Skeele, and Orlen, Gabriel and Avery, July 2;
Austin & Elliot, and The Brookside Project, July 9;
Katie Clarke & Larry LeBlanc and The Frost Heaves and Hales, July 16;
Steph Marshall, Pat & Tex LaMountain, and The John Lentz Trio, July 23;
Austin & Elliott and Joe Graveline, Nina Gross, and Dust Devils, with an open slot for a rained-out artist, July 30;
Small Change with two open slots for rained-out artists, Aug. 6;
Zydeco Connection with an open slot for a rained-out artist, Aug. 13;
Jim Eagan, Jennie McAvoy and The Klines, Aug. 20;
rained-out slots for affected artists, Aug. 27.
Montague Community Band at Peskeomskut Park - Montague
7 p.m.
June 8, 15, 22, 29; July 6, 13, 20, 27
Donations are accepted. Bring chairs.
Summer Concert Series - Amherst
5-8pm
June 27; July 11, 18, 25; August 1
Beats on the Boardwalk - Easthampton
Florence Summer Concert Series - Florence
Wednesday Folk Traditions at the Porter-Phelps-Huntington House Museum - Hadley - $12 for adults, $2 for children
Summer on Strong - Northampton
Summer Concert Series - South Hadley
The Bull Pen @ McCray’s Farm - South Hadley - Some $
Summer Concerts and Cruise Nights at Buttery Brook Park - South Hadley
May 25 with Ray Guillemette Jr.’s King Country at a special time of 12:30 p.m. All other concerts, unless noted, begin at 7 p.m. with Cobblestone Road, July 1; Ultimatum, July 8; Project 267, July 15; Jukebox Heroz, July 22; Agawam Night Out from 6-8 p.m. featuring a movie in the park at 8:30 p.m., July 24; Benny & the Jets, July 29; Retro Floyd, Aug. 5; Kix 100.9 Country Show, Aug.12; and General Gist at 6 p.m., Aug. 19.
Summer Concert Series - East Longmeadow
7 p.m
A Ray of Elvis , June 24; Trailer Trash followed by an Independence Day laser light show, July 3; Union Jack, July 8; 7Roads, July 15; Brass Attack, July 22; The 60’s Experience, July 29; Above the Treeline, Aug. 5 and Pridefalls, Aug. 12.
Holyoke Rotary Club’s summer concerts at Heritage State Park - Holyoke
5:30 p.m. to 8 p.m.
Lindsey LaBelle Band, Aug 5.
TBA, Aug. 12
TBA, Aug. 19.
Summit View Concerts on the site of Hamel’s Creative Catering - Holyoke - $5 Parking
Floyd Patterson Band, May 28;General Gist, June 4; Night Moves, July 2; Brass Attack, July 16; The Floyd Patterson Band, Aug. 13; and General Gist, Sept. 17.
Concerts in the Park - Springfield
6:30 p.m
The music begins with Dee Reilly on July 9 at the Carriage. Remaining concerts are held in the Forest Park Amphitheater with Petty Larceny Band, July 30; Skynyrd Hatchet, Aug. 6; Zac N Fried, Aug. 13; Jake Manzi Band, Aug. 20; Unforgettable Fire, Aug. 27; Bennie and the Jets, Sept. 3; and Floyd Patterson Band, Sept. 10.
Free Music Fridays at MGM Springfield - Springfield
Lawn Party @ The Landing at the Mass Mutual Center - Springfield
Sunday Night Concert Series - Westfield
6-8 p.m.
Floyd Patterson Band, June 7; Sweet Hitch Hiker, June 14; 7 Bridges Road, June 21; Studio 2, June 28; Cobblestone Road, July 12; Sarah the Fiddler, July 19; The Savage Brothers Band, July 26; The 413’s, Aug. 2; Brass Attack of Springfield, Aug. 9; and The Yacht Rock Band, Aug. 16.
Summer Concert Series - West Springfield
Storrowton Village gazebo July Concerts - West Springfield (Big E Fairgrounds)
7 p.m.
Ethel Lee Ensemble, July 9; Dan Kane & Friends, July 16; Richie Mitnick and Friends, July 23; and Sarah the Fiddler, July 30.