Dog Events in Chester, MA

Bring Fido out to this annual parade dressed in his favorite costume! In addition to a contest, there'll be local vendors, raffles, a kids' activity area and much more. The rain date is October 18.

Bring your costumed pup to participate in the dog costume parade at 12:00 PM! There will also be a beer garden, guess the weight of a pumpkin contest, plus shopping at 70+ retailers, crafters, local businesses, and vendors. The rain date is October 24th.

This dog-friendly Halloween celebration features trick-or-treating at downtown businesses, a canine costume contest with prizes, a puppy parade, and special offers at participating bars and restaurants. Dogs and their people can enjoy festive photo opportunities, giveaways and Halloween fun while supporting the Mohawk Hudson Humane Society through a portion of ticket proceeds.

Leashed dogs are welcome to this full-day event featuring local artisans, food trucks, live music, and seasonal drinks at Sons of Liberty Spirits Co. Dogs are permitted inside and outside.

Bring your Dachshund to compete in this exciting race event featuring multiple heats and a chance to earn the title of Connecticut’s fastest wiener dog! Participants are encouraged to bring treats and favorite toys to help cheer on their pups, while spectators can enjoy a fun-filled day supporting a nonprofit that provides holiday gifts to military families in need.

This dog-friendly costume parade invites pups to dress up and strut their stuff as part of a festive fall celebration. Guests can enjoy the parade along with the Port Jefferson Harvest Festival, featuring seasonal activities, vendors and entertainment all weekend.

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.

This dog-friendly fall festival features seasonal activities, local vendors, food and entertainment. Be sure to register Fido in the annual Port Jefferson Costumed Dog Parade during Saturday's festivities!

This dog-friendly 3K trail run and walk features optional obstacles, allowing pups and their people to run, walk or enjoy the course at their own pace. All obstacles are optional, making the event accessible for dogs of all abilities and comfort levels. Proceeds benefit NEADS Service Dogs and its service dog training programs.

Bring Fido to this Halloween-themed gathering of costumed canines and their owners! Watch adorable pups strut their stuff in creative and charming outfits for a chance to win fantastic prizes for the most creative costumes. Note that this event is only open to Fair Lawn residents.

Bring your pets for a photo day with Light & Lens Photography! All pets are welcome (please keep them leashed or in carriers). Each guest will receive one free digital file, with extra downloads and 8x10” prints available for just $5 each. Walk-ins are welcome, but reserving your spot online at is recommended!

A free Bergen County pet festival featuring adoptable pets, a Halloween costume parade, contests, puppy yoga, local vendors, family activities and more!

This dog-friendly Halloween event features decorated trunks from local pet-friendly businesses offering treats to pups and their people. Guests can also enjoy a dog costume contest, pie-eating contest, raffles, games and more.

Grab your sneakers and Fido's leash for a day on the trails. You can enroll in a 5K walk/run or a 1-mile fun run that welcomes all age levels. After the race, enjoy music, vendors, doggy demonstrations, and more at the Health & Fitness Fair. Costumes are encouraged (but not required).

Every Saturday and Sunday from May through October, leashed dogs are welcome at these live outdoor performances from talented local and regional bands across a variety of genres. Enjoy cold beer and savor delicious food. Guests are encouraged to bring lawn chairs and blankets. Start and end times vary by date; see their website for schedule.

Join the Van Cortlandt Park Alliance, Van Cortlandt House Museum, and the Urban Park Rangers for a free afternoon of family and dog-friendly fun! Enjoy creepy crafts, face painting, and spine-tingling stories with LINC on the museum lawn. At 3:00 PM, don’t miss the Annual Pup Parade & Canine Costume Contest. Pups can be registered from 2:00–2:45 PM or pre-register online. Cap off the evening with a Nocturnal Creatures and Wildlife Hike led by the Urban Park Rangers from 6:00–7:30 PM.

This dog-friendly Halloween block party invites families and their pets to enjoy trick-or-treating at local businesses along a car-free Elm Street. Guests can also enjoy spooky tunes from School of Rock, show off their costumes and take part in a free afternoon of Halloween fun for all ages.

Visitors and leashed dogs can enjoy a variety of attractions, including pumpkin picking, hay rides on weekends, a haunted corn maze, mini golf, jumbo jump pads, lawn games, wooden playlands, tractor pedal cars, and photo opportunities.

Visitors and leashed dogs can enjoy a variety of attractions, including pumpkin picking, hay rides (on weekends), a haunted corn maze, mini golf, jumbo jump pads, lawn games, wooden playlands, tractor pedal cars, and photo opportunities.

Don’t miss this annual event featuring a pet parade at 1 PM followed by a Halloween costume contest at 1:30 PM with prizes in categories like Best Overall, Scariest, Funniest, Cutest, Best Homemade, Best Pet & Owner Duo, Most Creative Use of Fur, and Best Barnyard Buddy. Delicious eats from food trucks and live music keep the fun going all afternoon for a paw-some autumn day! Please note that this is the only day that the farm welcomes dogs.