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    • 05
    Oct
    October 5, 2025 @ 10:00 am - 5:00 pm Broadway Bethpage, NY 11714

    Bethpage Street Fair

    Community street fair with vendors, music, kids’ activities and classic festival foods.
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    05
    Oct
    October 5, 2025 @ 10:00 am - 5:00 pm Park Blvd & Front St Massapequa Park, NY 11762

    Massapequa Park Fall Street Fair

    Artisans, food, live music, and kids’ activities along Park Boulevard in the heart of Massapequa Park.
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    10
    Oct
    October 10, 2025 @ 11:00 am - October 13, 2025 @ 6:00 pm Prime Ave & Main St Huntington, NY 11743

    Long Island Fall Festival

    Huntington’s biggest fall weekend: rides, music, 300+ vendors, beer & wine pavilion.
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    11
    Oct
    October 11, 2025 @ 10:00 am - October 12, 2025 @ 5:00 pm 1899 Park Blvd East Meadow, NY 11554

    Eisenhower Park Craft & Gift Fair

    Artisans, gifts, food stands and live entertainment at Field 8 in Eisenhower Park.
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    11
    Oct
    October 11, 2025 @ 11:00 am - October 12, 2025 @ 5:00 pm 40 Frost Mill Rd Mill Neck, NY 11765

    Mill Neck Manor Apple Festival

    Apples, cider, pies, crafts, rides and live entertainment on the historic manor grounds.
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    11
    Oct
    October 11, 2025 @ 11:00 am - October 13, 2025 @ 8:00 pm 152 The Arches Cir Deer Park, NY 11729

    Famous Food Festival: Taste the World

    100+ vendors, live music, games, and global street food at Tanger Outlets Deer Park.
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    11
    Oct
    October 11, 2025 @ 12:00 pm - 4:00 pm 3312 Montauk Hwy Sagaponack, NY 11962

    Wölffer Estate Annual Harvest Party

    Celebrate the season in style at the Wölffer Estate Annual Harvest Party, one of the Hamptons’ most anticipated fall traditions.
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    11
    Oct
    October 11, 2025 @ 6:30 pm - 10:00 pm 15975 County Rd 48 Cutchogue, NY 11935

    Annual Harvest Moon Dinner at Sannino Vineyard

    An elegant evening of wine, food, and live music under the harvest moon at Sannino Vineyard.
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    12
    Oct
    October 12, 2025 @ 10:00 am - 5:00 pm Main St & Peconic Ave Riverhead, NY 11901

    Riverhead Country Fair

    Agricultural exhibits, artisans, live music, food and family fun on the Peconic Riverfront.
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    12
    Oct
    October 12, 2025 @ 6:30 pm - 9:30 pm 185 Colonial Springs Rd Wheatley Heights, NY 11798

    RISE of the Jack O’Lanterns

    Thousands of glowing jack‑o’-lanterns on a breathtaking evening trail — a Long Island fall favorite.
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