Lee Founders Weekend

Friday September 19 – Sunday September 21

Celebrate Lee’s biggest weekend of the year with parades, live music, food vendors, fireworks, and family fun!

Join us for a festive weekend celebrating the rich history and vibrant spirit of Lee! Founders Weekend brings together locals and visitors alike with community pride in the heart of the Berkshires.

Weekend Highlights

Thursday, September 18

• The Barn at Lee presents Only Cowboys Get the Blues, 7:30pm, The Barn, 345 Spring St.

Friday, September 19

• Lee Historical Society Cemetery Talk– Fairmont Cemetery, 10-11am
• Taste of Lee – Main Street Closed to traffic 5:00-9:00pm
  Sample the best of our local restaurants and eateries during this delicious downtown tradition. Also: Live Music, Face Painting, Hay Wagon Rides, Touch-A-Truck, Race Car Display, CARRnival! Bounce-house & Games, Irish Dancers,
• Craft, Food, Vendor & Organization Fair: See list for details! 5-8pm, Church Park
• Beer Tent, 5-9pm, Live Music and Food
• The Barn at Lee presents Only Cowboys Get the Blues, 7:30pm, The Barn, 345 Spring St.
• 🎆 Spectacular Fireworks Display By Santore’s World Famous Fireworks, 8pm, – Visible from Main Street
  A spectacular kickoff to the weekend—bring a blanket and enjoy the show!

Saturday, September 20

• Feel Strong Yoga (8am) – Free for new students! (Registration Required), YogaLee, 62 Main St.
• Wildcat Main Street Mile Race – sponsored by LHMS Cross Country Team, 10am, Main Street: Lucky’s to Athletic Field. A high-energy race through downtown that kicks off the day’s festivities.
• Founders Hometown Parade! Parade Marshal: Peter Hofman. Immediately following the Mile, Main Street (Closed to Traffic 10-11am)
  Floats, performers, and local pride fill Main Street in this can’t-miss tradition. The parade will also be streamed live on CTSB Channel 1301 and available to watch on their website, CTSBTV.org.
• Craft, Food, Vendor & Organization Fair: See list for details! 9am-5pm, Church Park
  A lively market with handmade goods, local products, and community groups.
• Children’s Activities / Crafts / Sports, Sponsored by the Lee Youth Commission, 10:45am-3:30pm, All at The Athletic Field, including:
  • Performances by 413 Cheer and Gymnastics Unlimited, Bowey the Magic Clown, Terry A La Berry & Friends, Circus Skills Stations with Berkcirque
  • Lee Skate Park & Fingerboard Competition – All skill levels and all wheels welcome! 1:30pm
• Ongoing Activities:
  • Balloon Animals & Face Painting
  • Ninja Agility Challenge from Neighborhood Ninjas
  • Inflatable Obstacle Course from Army National Reserves
  • Bounce House
  • Hands on Activities with Berkshire Museum, Berkshire Music School, and Barrington Stage Company
  • Art Activities with Berkshire Art Center
  • Berkshire Bike & Board Bike Tune Up Station
  • Wildcat Sports
  • Airtime Clothing
  • Airen Wadsworth Family Resource Center information
  • Amanda Reis from Berkshire Hangout
• Food & Drinks: Cotton Candy from Lee Youth Commission, Ice Cream from the Pittsfield PD’s Copsicle Truck, Burgers and Hot Dogs from the Boy Scouts, Lemonade and Cookies from the LYA
• Lee Lions Founders Weekend Car Show, 11am-3pm, Lee Bank Parking Lot
  Admire vintage rides from across the region—plus live music by the Lucky Bucket Band.
• Antique Fire Truck Show also selling hamburgers & hotdogs, 11am-3pm, Lee Bank Parking Lot
  A family favorite featuring restored fire engines and historical vehicles.
• Lee Sons & Daughters of Italy G. Marconi Lodge #1620, Homemade Grinders under the Tent, 11am-1pm, Church Park
• Music in the Park: Concert by the Adamsville Ancients (11:15-11:45am) Drumming performance and hands-on workshop by Berkshire Rhythm Keepers (12-1pm), The Pavilion in the Park
• First Congregational Church Tours: Learn more about the church’s amazing steeple and “trompe l’oeil” style of painting, 11:30am-2pm, First Congregational Church
• Best Slider Burgers, grilled by Cafe Triskele and The Morgan House, 12:30-1:30pm, Church Park
• Author reading and book signing by Dan Sadlowski from his new children’s book Dear Wildflower, 1pm, Bliss Crumbs & Coffee, 77 Main St.
• Devonfield Inn Live Music Series: Happy Together Band, 3-4:30pm, Devonfield Inn, 85 Stockbridge Road
  BYO Chair and Refreshments of Choice!
• Harvest of the Heart: Movement, Energy, and Magic Autumnal Equinox Workshop (Registration Required), 4-6pm,YogaLee, 62 Main St.
  A two-hour gathering of ritual, somatic movement, and soulful connection led by Kerry McGinn and Sarah Brianna. Together we’ll honor the balance of light and shadow with ceremony, reflection, and community, leaving you grounded, inspired, and nourished.
• Old Fashioned Meeting House Supper – Tix: $15adults / $7 kids / under 5 free! 5:30pm, Lee Congregational Church
  A warm and welcoming evening meal served with tradition and community spirit.
• The Barn at Lee presents Only Cowboys Get the Blues, 7:30pm, The Barn, 345 Spring St.
• Live Music – Brian Benlein, 8-11pm, Locker Room Sports Bar

Sunday, September 21

• Knights of Columbus Raffle to benefit Berkshire charities, 8:45am-12pm, St. Mary’s Church
• Morning Yoga – Free for new students! 8:00am – Feel Good Flow. 9:30am – Feel Grounded, YogaLee Studio, 62 Main St. Registration required
• Craft, Food, Vendor & Organization Fair, 12-5pm, Church Park
• NEW! DOG PARADE Costumes Optional! Sponsored by Hearth & Hound. Live Music, Ice Cream, and More! – 1:00 PM 
  Leash up your pup and join the fun! Meet at the Part at 1pm, and the parade steps off at 1:15, headed to the Athletic Field for dog-friendly activities. Owners and their dogs are also welcome to skip the walk and meet at the Athletic Field. Costumes encouraged. Good dogs welcome. Smiles guaranteed.
• NEW! CORNHOLE TOURNAMENT Casual fun starts at 1pm, with tournament play at 2:15pm — a lively new addition to Founders Weekend where friendly competition meets community cheer, Athletic Field
• Duck Derby Race by the Lee Lions Club, 2pm, Housatonic River- Athletic Field
  Wrap up the weekend with this quirky and beloved Lee tradition—cheer on your [rubber] duck to victory!