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Attraction: Events

  • Pumpkintown USA – Connecticut

    Pumpkintown USA – Connecticut

    Pumpkintown USA

    Hampton, CT

    Pumpkintown-USA-ct
    From spooky season to holiday lights—the Pumpkinheads do it all.

    Pumpkintown USA
    • Address: 93 E High St, East Hampton, CT 06424
    • State: Connecticut
    • Website: www.pumpkintown.com

    Overview:
    Part fall attraction, part roadside oddity, Pumpkintown is a handmade village full of pumpkin-headed townsfolk. It’s been a family tradition in East Hampton since the early ’90s—and it’s every bit as weird and wonderful as it sounds.

    Why It’s Worth a Stop:
    Hop on the hayride through the woods and wave at the pumpkin mayor, the postman, the diner cook—even the local jailbirds. It’s silly, photogenic, and full of cider, donuts, and Halloween charm. And if you can’t get enough of the Pumpkinheads, come back for The Christmas Ride, when the forest gets a holiday makeover and the Pumpkin residents stick around for the season.

    What to Know Before You Go:
    • Fall season runs late September through Halloween.
    • The Christmas Ride opens Thanksgiving weekend and runs on select days through New Year’s Eve.
    • Tickets go fast—book in advance, especially for weekends.
    • Most activities are outdoors—check the forecast and bundle up.
    • Costumes welcome (but not required).

    Fun Fact:
    Each Pumpkinhead character has their own job, backstory, and personality. There’s even a full pumpkin fire department—and yes, they decorate for the holidays too.

  • Durham Fair – Durham, CT

    Durham Fair – Durham, CT

    Durham Fair

    Durham, CT

    Durham Fair - Durham, CT
    Since 1916, the Durham Fair has been Connecticut’s go-to for farm fun and fall vibes. 📷: Durham Fair

    Durham Fair
    • Address: 24 Town House Rd, Durham, CT 06422
    • State: Connecticut
    • Website: www.durhamfair.com

    Overview:
    Since 1916, the Durham Fair has been bringing small-town charm and big-time fun to Connecticut every fall. Held the last full weekend of September, it’s the state’s largest agricultural fair—and still proudly run by volunteers.

    Why It’s Worth a Stop:
    This is the kind of fair that has it all: live music on multiple stages, tractor pulls, midway rides, blue-ribbon animals, and more food than you can possibly sample in one visit. There’s also a discovery center, craft halls, and a farm museum if you want to slow down between funnel cakes.

    What to Know Before You Go:
    • Held annually the last full weekend of September.
    • Admission required; buy online or at the gate.
    • Free parking in satellite lots with shuttle service.
    • Wear comfy shoes—it’s a big fairground.
    • Some vendors are cash-only.

    Fun Fact:
    The fair is run entirely by volunteers—more than 1,500 of them pitch in every year to keep the tradition going.

  • Mystic Outdoor Art Festival – Mystic, CT

    Mystic Outdoor Art Festival – Mystic, CT

    Mystic Outdoor Art Festival

    Mystic, CT

    mystic-outdoor-art-festival-mystic-ct
    Art, music, and a mile of summer vibes in downtown Mystic. 📷: Mystic Chamber of Commerce

    Mystic Outdoor Art Festival
    • Address: Downtown Mystic, CT 06355 (Main Street to Mystic Seaport Museum)
    • State: Connecticut
    • Website: https://ctvisit.com/events/67th-mystic-outdoor-art-festival

    Overview:
    For one weekend every August, downtown Mystic fills with tents, artists, and creativity. This open-air festival stretches over a mile from Main Street to Mystic Seaport Museum, with the river nearby and artwork in every direction.

    Why It’s Worth a Stop:
    It’s a mix of laid-back and impressive—perfect for anyone who loves art, being outside, or just wandering with an iced coffee in hand. You’ll see everything from paintings and prints to woodwork and sculpture. There’s live music, stuff for kids to do, and a great excuse to spend the day in Mystic.

    What to Know Before You Go:
    • Usually held the second weekend in August.
    • Free to attend and super family-friendly.
    • Parking can be tricky—look for shuttle info or public lots.
    • Shops, snacks, and shade breaks are easy to find downtown.

    Fun Fact:
    This is the longest-running juried art festival in the Northeast—and it all started more than 65 years ago as a small local event.

  • Connecticut Garlic & Harvest Festival – Bethlehem, CT

    Connecticut Garlic & Harvest Festival – Bethlehem, CT

    Connecticut Garlic & Harvest Festival

    Bethlehem, CT

    garlic-festival-ct
    Garlic in every form—and a fall weekend you won’t forget. 📷: Connecticut Garlic & Harvest Festival

    Connecticut Garlic & Harvest Festival
    • Address: Bethlehem Fairgrounds, 384 Main St N, Bethlehem, CT 06751
    • State: Connecticut
    • Website: www.garlicfestct.com

    Overview:
    If you love garlic—or just love a good fall weekend—this is your kind of festival. Held every October in the little town of Bethlehem, it’s packed with food, music, crafts, and more garlic than you’ve probably ever seen in one place.

    Why It’s Worth a Stop:
    The second you get out of your car, you’ll know you’re in the right spot. The air smells like garlic bread, there’s something tasty around every corner, and it’s the kind of low-key event where everyone’s just there to have a good time (and eat). Try something wild, like garlic ice cream or fudge—or just grab a basket of garlic knots and wander.

    What to Know Before You Go:
    • Happens the second weekend of October.
    • Parking is free, but it fills up fast.
    • Bring cash—some booths don’t take cards.
    • It’s a rain-or-shine weekend, so dress for the weather.

    Fun Fact:
    The festival kicked off in 2004 with just a handful of vendors. Today, it’s one of Connecticut’s quirkiest (and tastiest) fall events.