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    Dog Events in Chesterfield, MA

    Here are the pet friendly events closest to Chesterfield. 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 West Hartford Pooch Plunge
    Aug 17

    West Hartford Pooch Plunge

    West Hartford, CT
    West Hartford Pooch Plunge All paws in the pool during this annual event! Bring Fido to enjoy some fun in the sun while splashing around alongside his pet companions. There will be two timed sessions offered. See Details
    Pet Friendly Bark in the Park: Wag Around the World Festival
    Aug 22

    Bark in the Park: Wag Around the World Festival

    Concord, NH
    Bark in the Park: Wag Around the World Festival Bring your pup to this dog-friendly summer festival. This unique “Wag Around the World” experience features food trucks inspired by flavors from around the globe, themed areas, live music, and family-friendly entertainment. There will hundreds of vendors, a car show, the Police vs. Fire Hometown Heroes Kickball Tournament, giveaways, raffles, and more! Every pre-purchased ticket includes a free vendor bag while supplies last. 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
    Aug 29

    Framingham Food Truck & Craft Beverage Festival at Eastleigh Farm

    Framingham, MA
    Framingham Food Truck & Craft Beverage Festival at Eastleigh Farm Leashed dogs are welcome at this outdoor festival that features a rotating lineup of food trucks serving diverse cuisine, craft beverage options, live entertainment, lawn games and local artisan vendors. It’s designed as a family-friendly celebration where friends and neighbors can enjoy great food and summer atmosphere together. See Details
    May 2–Aug 29

    Patio Party at Bear's Smokehouse BBQ

    New Haven, CT
    Patio Party at Bear's Smokehouse BBQ Spend the weekend enjoying live music (2 PM - 6 PM), barbecue, and outdoor fun at this family-friendly patio gathering. Guests can relax with happy hour specials, yard games, and great food while soaking up the atmosphere with their leashed pup! See Details
    Aug 29–30

    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–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
    Sep 9

    Annual Swim Pool Paw-ty at the Glen Rock Pool

    Glen Rock, NJ
    Annual Swim Pool Paw-ty at the Glen Rock Pool Register Fido for this annual gathering co-hosted by the Glen Rock NJ Dog Park and Glen Rock Parks and Recreation. Different times for sizes of dogs will be available to ensure safety and comfort. See Details
    Sep 12

    Annual Animal Blessing

    Redding, CT
    Annual Animal Blessing Bring your pet out for an afternoon of walking on the beautiful property while visiting with other animal lovers and their pets. Join in family activities followed by a traditional animal blessing and special guest speakers. The blessing will take place from 12:00–1:00 PM. See Details
    Sep 12–13

    Garlic Festival at Waterdrinker North Fork

    Riverhead, NY
    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. See Details
    Sep 13

    Pups in the Pool at Spook Rock Swimming Pool

    Suffern, NY
    Pups in the Pool at Spook Rock Swimming Pool Let your pups splash, paddle and play in the pool—just for them! Dogs must be accompanied by someone 18+ and have written proof of rabies vaccination. 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 19

    Bark in the Park: In Memory of Tyler

    Bethel, CT
    Bark in the Park: In Memory of Tyler This special event will be held in memory of the dog park founder's dog, Tyler. It'll be a great way to celebrate his legacy and impact while Fido enjoys the park with other pups and enjoys pup cups from their dog menu. The event will also have pet-focused vendors, food trucks, raffles, live music, demonstrations and more. See Details
    Sep 20

    Operation Delta Dog 5K Run to Rescue

    Nashua, NH
    Operation Delta Dog 5K Run to Rescue Run or walk this peaceful (but fun!) 5K through the beautiful Mine Falls for a good cause. Operation Delta Dog rescues dogs and trains them to be service dogs for veterans - all at no cost to our veterans! This is one of the few 5K events in the area that welcomes you to run with your four-legged leashed running partner. There will be prizes waiting for all dog finishers, as well as special awards for best dressed pups, matching outfits with their human runners, fastest human/dog team and more. 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 26

    5K Chamber Challenge

    Meriden, CT
    5K Chamber Challenge Join a community 5K supporting local organizations focused on recovery and education. Participants of all fitness levels can walk, run, or jog while enjoying a fun, family-friendly event featuring a Kids’ Fun Run and opportunities for businesses and community members to get involved. Leashed pets are welcome to join the challenge. 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
    Oct 4

    Baypath Humane Society Annual Paws & Claws 5K

    Hopkinton, MA
    Baypath Humane Society Annual Paws & Claws 5K A charity 5K run/walk that welcomes runners, walkers, and their dogs to Hopkinton State Park to raise funds for the Baypath Humane Society. The event features a Doggie Division for participants running or walking with their dogs, vendor village, and community activities supporting animals in need. See Details
    Oct 4

    Annual Pet Rock Festival

    Lancaster, MA
    Annual Pet Rock Festival Bring Fido for a fun afternoon of live music, vendors, food, contests, and more than 150 animal organizations broadcasting their causes. Attendees can meet adoptable pets, learn from educational exhibits, and connect with animal welfare groups working to protect and support animals. The event also hosts contests, demonstrations, and interactive activities to engage both pets and their owners. See Details
    Chesterfield, MA, US