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.

Jun 6

Woofstock Music Festival & 5K

Scotia, NY

Woofstock Music Festival & 5K Bring Fido to this annual groovy festival featuring fun for the whole family! The day kicks off with a 5K run or walk at 10 AM, followed by a fun festival. Attendees can listen to live music, shop from vendors, chow down on a bite from food trucks and sip on refreshing beverages. This outdoor event is one of the largest in the region and is critical to supporting the mission of the Animal Protective Foundation. See Details

Jun 6

Worcester Food Truck & Craft Beverage Festival

Worcester, MA

Worcester Food Truck & Craft Beverage Festival Leashed dogs are welcome at this annual festival where guests can savor delicious bites from the city's top food trucks, enjoy a selection of refreshing craft beverages, and listen to entertainment from local performers. See Details

Jun 6

Wilkins Dog Pawty

Barre, VT

Wilkins Dog Pawty Bring your furry friend for a tail-wagging good time! Meet and mingle with other pups, snap adorable pet photos, grab a doggy gift bag, and meet lovable adoptable dogs from Passion 4 Paws. See Details

Jun 6

Dog-Friendly Day Retreat: Unleash Your Summer

Simsbury, CT

Dog-Friendly Day Retreat: Unleash Your Summer Experience a one-of-a-kind retreat designed to strengthen the bond between you and your dog through wellness, adventure and connection. Guests can enjoy activities like dog yoga, meditation, training sessions, hiking, paddling, and group swim time, along with relaxing moments around campfires and creative workshops and educational seminars. See Details

Jun 7

Annual Pets in the Park New Milford

New Milford, CT

Annual Pets in the Park New Milford Enjoy a family-friendly pet celebration filled with shopping, adoptable animals, rescue groups, entertainment, and activities for animal lovers and their furry companions. Guests can browse pet vendors, meet local rescues, participate in costume contests and animal blessing ceremonies, and enjoy food, treats, and community fun throughout the day. The rain date is June 14th. See Details

Jun 7

South Windsor Pet Palooza

South Windsor, CT

South Windsor Pet Palooza Bring Fido to check out the palooza, featuring vendors, pet adoptions, demonstrations, educational booths and pet contests. Food trucks will also be on site. See Details

Jun 6–7

Benson’s Pet Center DockDogs Event

Clifton Park, NY

Benson’s Pet Center DockDogs Event High-flying dogs make a splash at this nationally sanctioned DockDogs competition! Spectators are welcome, and dog-owning attendees may register their pups to compete in Big Air, Extreme Vertical, Speed Retrieve, or the combined Iron Dog challenge in a fun, family atmosphere. See Details

Jun 7

The Great Country Mutt Show

Lakeville, CT

The Great Country Mutt Show Celebrate dogs of every breed, mix and personality at this fun-filled community dog show! Inspired by classic Westminster-style competitions, the event features lighthearted contest categories, pet-and-owner activities, live entertainment, food vendors, shopping, and family-friendly fun throughout the day. See Details

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

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

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