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Dog Events in Pittsfield, MA

Here are the pet friendly events closest to Pittsfield. 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 Party on the Porch

Jun 19

Annual Party on the Porch

Ballston Lake, NY

Annual Party on the Porch

Held on the porch with live music from local band Grand Central Station, the evening features free pizza and ice cream, drinks available for purchase, and a 50/50 raffle, all set against a laid-back, family-friendly backdrop. Attendees are encouraged to bring lawn chairs and enjoy a night of great music, food, and community spirit.

Pet Friendly Bark in the Park at the Springfield Armory National Historic Site

Jun 20

Bark in the Park at the Springfield Armory National Historic Site

Springfield, MA

Bark in the Park at the Springfield Armory National Historic Site

Leashed dogs are welcome during this special event. Activities include a picnic with your pup, completing a Bark Ranger activity booklet, a pup cup station, making a bandana and more!

Jun 20

Hudson Valley Food Truck Festival

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.

Jun 20

Summer Night on The Hill

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.

Jun 21

Father’s Day Mini Golf

Father’s Day Mini Golf

Celebrate Father’s Day with a fun-filled afternoon of mini golf, live music, and family-friendly entertainment. Guests can enjoy a free round of mini golf, dance along to live rock and roll, and grab food from on-site vendors. Dogs are welcome to join the festivities, making it a great outing for the whole family.

Jun 20–21

A Man's Best Friend

A Man's Best Friend

Celebrate dads and their dogs with a fun, enrichment-style experience. Dogs can enjoy a special themed treat while also participating in a creative activity to make a keepsake gift for their person. This add-on experience is available for dogs attending daycare or boarding and is designed to bring extra joy, engagement, and celebration to their stay.

Jun 23

Bark in the Park with the Worcester Bravehearts

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.

Jun 28

Fairfield Dog Days hosted by Pet Pantry Warehouse

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.

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.

Jul 4

Town of Killington 4th of July Parade

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.

Jul 25

Botanicals and Brews at Lilac Hedge Farm

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.

Jun 5–Jul 31, except Jul 3

Live Concert Series at Ridge Hill

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.

Aug 15–16

Annual Seafood & Wine Festival at Robibero Winery

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.

Aug 22

Dog-Friendly Day Retreat: Tails of Adventure

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.

Jul 4–Sep 5

Cooler in the Mountains Summer Concert Series

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.

Sep 12–13

Garlic Festival at Waterdrinker North Fork

Garlic Festival at Waterdrinker North Fork

Celebrating the harvest season, this dog-friendly festival features live music, a vendor market with garlic-inspired goods, food trucks, and activities across the 40-acre farm. Attendees can enjoy sunflower fields, pumpkin picking, a corn maze, a garlic scavenger hunt, and a musical hayride. Unique treats like garlic ice cream and garlic butter roasted corn will be available.

Select dates, Mar 29–Sep 19

Bark in the Park with the Worcester Red Sox

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.

Sep 26

Steampunk Day at Old Rhinebeck Aerodrome Air Show

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.

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.

Oct 3

Dog-Friendly Day Retreat: Paws 'N' Reflect

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.

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Pittsfield, MA, US