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    Dog Events in Bennington, VT

    Here are the pet friendly events closest to Bennington. Use the links below to get details on each event, print directions, look at pictures, and even read reviews of last year’s event.

    Pet Friendly Annual Pawpawpalooza
    Jun 13

    Annual Pawpawpalooza

    Newtown, CT
    Annual Pawpawpalooza Gather the whole family for a fun-filled day celebrating pets and bringing the community together. There will be on-site pet adoptions, a vendor fair, food trucks, a low-cost rabies and microchip clinic and more. So, whether you're hoping to adopt a furry friend or take part in pet-themed activities, this lively event has something for everyone! See Details
    Pet Friendly Little Poland Festival
    Jun 14

    Little Poland Festival

    New Britain, CT
    Little Poland Festival Your pup is welcome to join you, just make sure to keep him on a leash! With leaping folk dancers, live music, arts and crafts, unique shopping, amazing food, costumed characters, carnival rides and activities for the young and young at heart, this festival is one of the fastest-growing family-friendly festivals of its kind in Connecticut. The festival is held right in the heart of New Britain's historic Little Poland neighborhood where you can find over 100 businesses! See Details
    Jun 20

    Hudson Valley Food Truck Festival

    Poughquag, NY
    Hudson Valley Food Truck Festival Spend the day enjoying a lively outdoor festival filled with food trucks, live music, local brews, artisan vendors, and family-friendly activities. Well-behaved dogs and owners can explore farm attractions, lawn games, hay rides, a petting zoo, and a dedicated dog park while sampling a wide variety of food and drinks available for purchase. See Details
    Jun 23

    Bark in the Park with the Worcester Bravehearts

    Worcester, MA
    Bark in the Park with the Worcester Bravehearts Take Fido out to a game! On this day only, dogs are invited along to watch the Worcester Bravehearts baseball game. See Details
    Jul 4

    Town of Killington 4th of July Parade

    Killington, VT
    Town of Killington 4th of July Parade Celebrate Independence Day with a classic small-town parade that welcomes community participation from residents, businesses, organizations and visitors. Parade highlights include creative family-friendly floats, decorated bicycles for children, walking groups, and plenty of patriotic spirit. See Details
    Jul 25

    Botanicals and Brews at Lilac Hedge Farm

    Rutland, MA
    Botanicals and Brews at Lilac Hedge Farm New England Plant Expo presents an exotic plant market to enjoy with your four-legged friend. There'll be a variety of plants as well as botanically themed artisans and crafters. Food trucks are also available on site. See Details
    Aug 15–16

    Annual Seafood & Wine Festival at Robibero Winery

    New Paltz, NY
    Annual Seafood & Wine Festival at Robibero Winery Gather your family and friends for a lively celebration of coastal flavors, fine wine, and sweeping vineyard scenery. This festive outdoor experience features seafood and wine stations, live DJ entertainment, games, activities, and artisan vendors throughout the grounds. Well-behaved dogs are welcome to take part in the day. A portion of the proceeds will be donated to the American Cancer Society. See Details
    Aug 22

    Dog-Friendly Day Retreat: Tails of Adventure

    Simsbury, CT
    Dog-Friendly Day Retreat: Tails of Adventure Enjoy a one-of-a-kind wellness retreat designed for both you and your dog, focused on strengthening your bond through shared experiences. The day includes a mix of adventure and relaxation with activities like dog yoga, meditation, training sessions, hiking, paddling, and group swim time. Guests can also take part in workshops, crafts, and educational seminars. See Details
    Jul 4–Sep 5

    Cooler in the Mountains Summer Concert Series

    Killington, VT
    Cooler in the Mountains Summer Concert Series Enjoy outdoor concerts each Saturday at the resort with top local and national acts! Bring a lawn chair, beach blanket, friends and Fido for a relaxing mountain afternoon. The Snowshed Umbrella bar serves craft Vermont beer, cocktails and snacks during the show, weather permitting. While leashed dogs are welcome, keep them under control and away from concrete areas, as they aren't permitted on the umbrella bar deck. See Details
    Select dates, Mar 29–Sep 19

    Bark in the Park with the Worcester Red Sox

    Worcester, MA
    Bark in the Park with the Worcester Red Sox On select dates throughout the season, bring your furry friend for a day of fun and baseball! Check their website for full schedule and dog-friendly game days. See Details
    Sep 26

    Steampunk Day at Old Rhinebeck Aerodrome Air Show

    Red Hook, NY
    Steampunk Day at Old Rhinebeck Aerodrome Air Show On Steampunk Day at the Old Rhinebeck Aerodrome Air Show, aviation history meets imaginative Victorian‑era science‑fiction fun. In addition to the museum’s usual airshow flying schedule, the themed day includes opportunities to see vintage planes in flight alongside steampunk characters and costumes, and creative activities inspired by steampunk culture. Please note that the airplanes can be very noisy, and there could be an occasional gunshot or explosion. See Details
    Sep 24–27

    Canine Camp Getaway East Durham

    East Durham, NY
    Canine Camp Getaway East Durham Enjoy the ultimate dog vacation in the scenic Catskill Mountains! Grab your dog for a unique, all-inclusive vacation with activities ranging from agility, hiking, and pet-friendly pool fun to lure coursing, vet seminars, nose work, disc dog, canine freestyle dance, barn hunt, Therapy Dog training and testing, and so much more! At night, enjoy dog-friendly evening entertainment like country line dancing, movie night and a musical comedy show. No formal training is required; all friendly dogs are welcome. See Details
    Oct 3

    Dog-Friendly Day Retreat: Paws 'N' Reflect

    Simsbury, CT
    Dog-Friendly Day Retreat: Paws 'N' Reflect Experience a wellness-focused retreat designed for you and your dog, centered on strengthening your bond through shared activities and relaxation. The experience includes a mix of adventure and enrichment like dog yoga, meditation, training, hiking, paddling, and group swim time, along with creative workshops and educational seminars. See Details
    Sep 26–Oct 4

    Grape Stomping Festival at Robibero Winery

    New Paltz, NY
    Grape Stomping Festival at Robibero Winery Get ready for a lively vineyard celebration featuring grape stomping, live music, lawn games, and cozy bonfires in a scenic outdoor setting. Guests can enjoy wine tastings, sangria, craft beverages, wood-fired pizza, and artisan snacks while relaxing on the lawn. Families and pets are welcome to join the fun, and covered seating is available rain or shine. See Details
    Oct 11

    Annual Pets in the Park Danbury

    Danbury, CT
    Annual Pets in the Park Danbury Enjoy a family-friendly celebration for pets and animal lovers featuring shopping, demonstrations, rescue groups, adoptions, and plenty of activities for both people and their furry companions. Guests can bring their leashed pets to participate in a lively pet costume contest, enjoy an animal blessing ceremony, browse local vendors, and grab food and treats throughout the day. The event also includes face painting and community activities, with a portion of admission proceeds benefiting local animal shelters. See Details
    Aug 8–9 & Oct 10–11

    Annual Summer and Fall Art in the Park

    Rutland, VT
    Annual Summer and Fall Art in the Park Enjoy a day of art, music, and family fun at this annual festival featuring fine artists, craftspeople, specialty foods, and kid-friendly activities. Leashed dogs are welcome to join. See Details
    Jun 20–Oct 18, weekends only

    Old Rhinebeck Aerodrome Air Shows

    Red Hook, NY
    Old Rhinebeck Aerodrome Air Shows Visitors and leashed dogs are welcome each weekend to watch thrilling flight demonstrations featuring authentic historic aircraft, and enjoy educational exhibits. Bench and bleacher seating are available, and a limited number of camp chair rentals. Concessions are also available for purchase. Please note that the airplanes can be very noisy, and there could be an occasional gunshot or explosion. See Details
    Dec 5

    Jingle Bell Run - Central MA

    Worcester, MA
    Jingle Bell Run - Central MA The Arthritis Foundation’s race is the original festive race for charity with your pup. It’s where you can strut your stuff in your favorite holiday costume. Bring a team of friends, family, and co-workers to run or walk. Please ensure your dog is kept on a leash. Check-in starts at 8:00 AM and the race begins at 9:30 AM. See Details
    Dec 6

    Jingle Bell Run - Capital Region, NY

    Saratoga Springs, NY
    Jingle Bell Run - Capital Region, NY The Arthritis Foundation’s race is the original festive race for charity with your pup. It’s where you can strut your stuff in your favorite holiday costume. Bring a team of friends, family, and co-workers to run or walk. Please ensure your dog is kept on a leash. Check-in starts at 9 AM and the race begins at 10 AM. See Details

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    Bennington, VT, US