Ongoing

Gilmore Weekend Fun!

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Create Escape Studio 143 West Street - Unit U, New Milford

Take a Break and Create with us! It's more than a souvenir... It's an experience. Enjoy creating Gilmore-inspired art in our comfortable and welcoming DIY art studio. Located just a […]

$25

Drop-In Dragonfly Pour Painting Experience

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Gallery 25 in the Historic Train Station 11 Railroad Street, New Milford

Inspired by the iconic Dragonfly Inn of Stars Hollow, this playful and creative painting experience lets you pour your heart into a one-of-a-kind abstract dragonfly! Using fluid acrylics and pour painting […]

$35

🌼 Watercolor Workshop: 1000 Yellow Daisies

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Gallery 25 in the Historic Train Station 11 Railroad Street, New Milford

Paint your own grand romantic gesture! Inspired by the unforgettable Gilmore Girls moment when Lorelai asks for “1000 yellow daisies,” this whimsical watercolor class brings that dreamy energy to life on paper. […]

$45.00

Paint a Gilmore Girls Bandstand Picture Frame

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Village Center for the Arts 12 Main Street, New Milford

Paint a Bandstand Picture Frame September 12, 13, & 14 10:30-12:30 / 1:00-3:00 / 3:30-5:30 Paint a handmade bandstand picture frame the Gilmore Girls would be proud of. This comes […]

$40.

🎨 Paint Your Own Watercolor Bookmark!

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Village Center for the Arts 12 Main Street, New Milford

🎨 Paint Your Own Watercolor Bookmark!September 12, 13 & 14 | 11:00 AM – 6:00 PM Drop in any time and get creative at this free, all-ages event—no experience needed! […]

Free

New Milford Historical Society – Blow out sale!

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New Milford Historical Society 6 Aspetuck Ave, New Milford

Blow out sale in the bank building during the Weekend in the Life event

Free

Paint the Gazebo/Bandstand – Friday

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Create Escape Studio 143 West Street - Unit U, New Milford

Paint the Gazebo in All Its Autumn Glory Nothing says cozy small-town charm quite like the town gazebo—and New Milford's feels straight out of Stars Hollow. Join us for a […]

$40.00

Candlewood Valley Country Club: Bourbon and Cigar Tasting

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Candlewood Valley Country Club 401 Danbury Rd, New Milford

Savor the perfect fall evening at Candlewood Valley Country Club! Join us on Friday, September 12, 6:30–8:30 PM for Bourbon and Cigars (Fall Edition), presented by 9th and Madison Cigar Company. Enjoy light appetizers, a premium cigar, and exclusive tastings from Woodford Reserve, Widow Jane, and American Metal Distillery — plus a few surprise bourbons! 🍂🥃
Reserve your spot today — limited availability!

$85