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  • Sip & Paint: New Milford Bandstand @ Gallery 25

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

    Back by popular demand! Join local favorite Liz for a fun-filled evening of painting, sipping, and creativity as we bring the iconic New Milford Bandstand to life on canvas. This class was a hit at the last convention—and now it’s your turn to paint this beloved local landmark! Whether you're a beginner or a seasoned painter, Liz […]

    $55

  • Autumn Wine Glass Painting

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

    Enjoy a fun, festive, and creative evening out with friends, painting wine and/or cocktail glasses. Reservations must be made by 9/9 Choose from a style of wine glass or pint glass at registration. 2 glasses: $45 per person 1 glass: $32 per person Registration can not be shared. Thank you for your cooperation. BYOB and […]

    $45

  • 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 techniques, you'll create your own vibrant and whimsical dragonfly masterpiece—no experience needed. This drop-in event is perfect for Gilmore Girls fans, art lovers, and anyone who just […]

    $35

  • 🌼 Watercolor Workshop: 1000 Yellow Daisies

    Featured
    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. Join Liz at Gallery 25 as part of A Weekend in the Life, and paint your own field of yellow blooms in this relaxed, beginner-friendly workshop. […]

    $45.00

  • Paint a Gilmore Girls Bandstand Picture Frame

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    Village Center for the Arts 12 Main Street, New Milford, CT

    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 with everything you need to paint and create a memory of your time in Stars Hollow! Each one is a hand made ceramic bandstand ready […]

    $40.

  • 🎨 Paint Your Own Watercolor Bookmark!

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    Village Center for the Arts 12 Main Street, New Milford, CT

    🎨 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! Walk into our "Stars Hollow" like picturesque art center and get to know our friendly crew! Design a one-of-a-kind bookmark that even Rory Gilmore would […]

    Free

  • New Milford Historical Society – Blow out sale!

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    New Milford Historical Society 6 Aspetuck Ave, New Milford, CT

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

    Free

  • Paint the Gazebo/Bandstand – Friday

    Featured
    Create Escape Studio 143 West Street - Unit U, New Milford, CT, United States

    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 step-by-step painting workshop where you’ll capture the gazebo surrounded by golden leaves and crisp autumn beauty. No painting experience needed—just bring your love of fall, […]

    $40.00

  • Candlewood Valley Country Club: Bourbon and Cigar Tasting

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    Candlewood Valley Country Club 401 Danbury Rd, New Milford, CT

    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

  • Layers of Me: A Mindful Art & Sound Journey

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    JCC in Sherman 9 Route 39 South, Sherman, CT

    Hosted by Amber Vlangas, MAT of Mindful Art and Sound Peel back or build up your layers. Meet yourself with creativity, curiosity and compassion. Join us for a creative 2-hour workshop where we’ll explore the parts of ourselves that are often left unspoken - through intuitive art-making, gentle sound meditation, reflection, and mindful presence. No […]

    $45