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Over 40 Events and Things to do in Pittsfield, MA

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Yoga in the Valley XV
Tomorrow at 7:00 PM
Peekskill · Valley Greens
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Yoga in the Valley XV
Tomorrow at 7:00 PM
Peekskill · Valley Greens
ROLL DEEP
Fri, Jul 17, 10:00 PM
Bridgeport · Creative Venue & Rentals
ROLL DEEP
Fri, Jul 17, 10:00 PM
Bridgeport · Creative Venue & Rentals
REASONS
Sat, May 30, 9:00 PM
Bridgeport · 40 Logan St
REASONS
Sat, May 30, 9:00 PM
Bridgeport · 40 Logan St
Collectibles Extravaganza - Comics Toys Records June 27-28 Boxboro MA
Sat, Jun 27, 9:00 AM
Boxborough · Boxboro Regency
Collectibles Extravaganza - Comics Toys Records June 27-28 Boxboro MA
Sat, Jun 27, 9:00 AM
Boxborough · Boxboro Regency
Frosty Brews & Vegan Treats 2026
Sun, May 31, 1:00 PM
Hudson · Clover Road Brewing Company
Frosty Brews & Vegan Treats 2026
Sun, May 31, 1:00 PM
Hudson · Clover Road Brewing Company
Gibbet Hill Farm Dinner • July 15
Wed, Jul 15, 6:00 PM
Groton · Gibbet Hill Grill
Gibbet Hill Farm Dinner • July 15
Wed, Jul 15, 6:00 PM
Groton · Gibbet Hill Grill
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The Fix Marlborough Patio Party Summer Kickoff!
Sunday at 3:00 PM
Marlborough · The Fix Burger Bar
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The Fix Marlborough Patio Party Summer Kickoff!
Sunday at 3:00 PM
Marlborough · The Fix Burger Bar
24 KARATS RAVING
Sat, Jul 25, 2:00 PM
Bridgeport · 40 Logan St
24 KARATS RAVING
Sat, Jul 25, 2:00 PM
Bridgeport · 40 Logan St
Milford 3rd Annual Fall Craft Fair
Sun, Oct 18, 11:00 AM
Milford · VFW Post 4368
Milford 3rd Annual Fall Craft Fair
Sun, Oct 18, 11:00 AM
Milford · VFW Post 4368
Stress Management 1 Day Workshop |Bridgeport, CT
Thu, Jun 11, 9:00 AM + 1 more
Bridgeport · For venue details reach us at info@learnerring.com
Stress Management 1 Day Workshop |Bridgeport, CT
Thu, Jun 11, 9:00 AM + 1 more
Bridgeport · For venue details reach us at info@learnerring.com
Thrills & Chills Book Fair
Sun, Jul 12, 12:00 PM
Middletown · Aspire Brewing
Thrills & Chills Book Fair
Sun, Jul 12, 12:00 PM
Middletown · Aspire Brewing
Homeward Bound
Thu, Jun 4, 5:00 PM
Stratford · Two Roads Area Two Tasting Room & Experimental Brewing
Homeward Bound
Thu, Jun 4, 5:00 PM
Stratford · Two Roads Area Two Tasting Room & Experimental Brewing
New England Christmas Festival 2026
Fri, Nov 6, 9:00 AM
Uncasville · Mohegan Sun Earth Expo & Convention Center
New England Christmas Festival 2026
Fri, Nov 6, 9:00 AM
Uncasville · Mohegan Sun Earth Expo & Convention Center
Speed Dating Ages 40-55 in Norwalk, CT at Odeen’s BBQ Restaurants
Wed, Jun 17, 7:00 PM
Norwalk · Oak Hills Park Golf Course
Speed Dating Ages 40-55 in Norwalk, CT at Odeen’s BBQ Restaurants
Wed, Jun 17, 7:00 PM
Norwalk · Oak Hills Park Golf Course
The Normal Heart by Larry Kramer
Fri, Jun 12, 7:00 PM + 7 more
Peekskill · Studio Theater in Exile
The Normal Heart by Larry Kramer
Fri, Jun 12, 7:00 PM + 7 more
Peekskill · Studio Theater in Exile
Singles Mixer | Speed Dating & PAINT N SIP @Pasta Della Nonna in Goshen,NY
Thu, May 28, 7:00 PM
Goshen · 1753 NY-17M
Singles Mixer | Speed Dating & PAINT N SIP @Pasta Della Nonna in Goshen,NY
Thu, May 28, 7:00 PM
Goshen · 1753 NY-17M
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ITIL 5 Training This Month in Bridgeport, CT – Enroll Now
Thu, May 28, 9:00 AM + 4 more
Bridgeport · 1000 Lafayette Blvd
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ITIL 5 Training This Month in Bridgeport, CT – Enroll Now
Thu, May 28, 9:00 AM + 4 more
Bridgeport · 1000 Lafayette Blvd
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Only a Few Seats Left for ITIL 4 in Bridgeport, CT – Register Today
Thu, May 28, 9:00 AM
Bridgeport · 1000 Lafayette Blvd
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Only a Few Seats Left for ITIL 4 in Bridgeport, CT – Register Today
Thu, May 28, 9:00 AM
Bridgeport · 1000 Lafayette Blvd
Andy McKee
Fri, Jun 12, 8:00 PM
Fairfield · StageOne at FTC
Andy McKee
Fri, Jun 12, 8:00 PM
Fairfield · StageOne at FTC
Livingston Taylor
Thu, Jun 25, 8:00 PM
Fairfield · StageOne at FTC
Livingston Taylor
Thu, Jun 25, 8:00 PM
Fairfield · StageOne at FTC

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