Dog Events in Lenox, MA

Here are the pet friendly events closest to Lenox. 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

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 6

MedVet Norwalk Open House

Norwalk, CT

MedVet Norwalk Open House Join a family-friendly hospital open house to go behind the scenes, meet veterinary specialists, and learn more about 24/7 emergency and specialty pet care services. Pets are welcome to join their owners for a day of interactive activities, including free microchipping, paw print art, educational stations, kids’ vet-themed fun, refreshments, and giveaways. 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 20

Summer Night on The Hill

Yonkers, NY

Summer Night on The Hill Celebrate the start of summer with Fido at a free outdoor block party featuring live music, family-friendly activities, shopping promotions, giveaways, roaming entertainment, interactive games, photo opportunities, food, drinks, and special experiences from local retailers and restaurants. 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

Jun 28

Fairfield Dog Days hosted by Pet Pantry Warehouse

Fairfield, CT

Fairfield Dog Days hosted by Pet Pantry Warehouse Get ready for an entertaining event that your pup and the whole family will enjoy. The day will be filled with pet-centric activities, competitions and vendors. The event proceeds will be donated to local animal shelters and rescues, including Adopt-A-Dog, Operation Hope, and Team Woofgang & Co. See Details

Jun 27–28

Annual East Hampton Art Affair

East Hampton, NY

Annual East Hampton Art Affair Leashed dogs are welcome at this annual fair that features local and national artists showcasing a diverse range of fine art, including sculptures, jewelry, woodwork, paintings wearable art and more. Visitors will have the chance to meet artists, explore their techniques, commission custom pieces, and learn about their inspirations. 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

Jun 5–Jul 31, except Jul 3

Live Concert Series at Ridge Hill

Yonkers, NY

Live Concert Series at Ridge Hill Enjoy free outdoor concerts every Friday (no show July 3rd) with Fido, featuring live performances from a variety of musical genres in a lively community setting. Guests are encouraged to bring lawn chairs and relax while enjoying an evening of music, food, and drinks from nearby restaurants and on-site beverage vendors. Seating is available on a first-come, first-served basis, and concerts may be canceled in the case of inclement weather. 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