Dog Events in Chester, MA

Leashed dogs are welcome the first Friday of every month from May through November when businesses are encouraged to stay open late and the streets come alive with food trucks, live performances, art displays and other activities.

Four-legged friends are invited to this annual event featuring cars, brews and good friends! Owners and their furry companions can grab a beer in the taproom and lounge beside a fire pit on the outdoor patio. The car show will be hosted in the private space behind the brewery. This event is run by and for furries. However, you do not need to be a furry to attend.

Bring the whole family and your well-behaved pup to a holiday market featuring 15+ food trucks, 100+ vendors, live music, Police K9 demonstrations, a free community dog show, a Kid Zone, Holiday Market, two Christmas trains, Santa and Mrs. Claus, raffles, giveaways and more. A free shuttle runs from Big Jim’s Home Center to Rollins Park, and dogs are allowed on the shuttle. Dogs may take photos with Santa, but aren't permitted on the Christmas trains. Dogs must be well-behaved, healthy, and current on vaccinations. Please use a non-retractable leash no longer than 4'.

Lace up your sneakers and grab Fido's leash to hit the course. Please note your leashed furry friend must show up-to-date rabies vaccinations. The course begins at the Banks Humane Education Center to the grounds of St Paul's School and back to the SPCA. Register by November 1st to receive a free race t-shirt!

Capture holiday memories with your furry friend to look back on picture-perfect moments. Each session lasts approximately 15 minutes. Two digital image files and a donation to the charity are included in your session fee! You can also purchase prints and additional digital images.

Bring your furry friends for a festive photoshoot with Santa! There will also be other photo stations around the barn you can utilize to take personal photos with your camera. Refreshments provided by the North Stonington Lions Club. Please make an appointment to see Santa.

All pets are welcome to come get a holiday photo! All attendees will receive free treats.

A dog-friendly Thanksgiving tradition! Participants can choose a 4-mile run or a 2-mile walk, making it a festive activity for all ages and abilities. Every participant receives a hat and apple pie, while preregistered participants also receive a long-sleeve race shirt. Race-day registration and giveaways are available while supplies last.

Bring Fido along to this fun-filled morning to walk or jog! Pups participating in the 2K pet walk will receive a special doggie treat at the finish line from Tater Bear Treats. Please bring an unwrapped toy to help spread holiday cheer for the Toys for Tots program.

This annual signature event of the Williamstown Holiday Walk begins with line-up and costume contest judging at 1:30 PM at the Falk Science Quad at Williams College. Dog owners are welcome to deck their hounds in festive attire for prizes in categories: Small, Medium, Large & Family Troupe. The parade will then head down Spring Street.

The Arthritis Foundation’s race is the original festive race for charity with your pup. It’s where you can strut your stuff in your favorite holiday costume. Bring a team of friends, family, and co-workers to run or walk. Please ensure your dog is kept on a leash. Check-in starts at 8:00 AM and the race begins at 9:30 AM.

The Arthritis Foundation’s race is the original festive race for charity with your pup. It’s where you can strut your stuff in your favorite holiday costume. Bring a team of friends, family, and co-workers to run or walk. Please ensure your dog is kept on a leash. Check-in opens at 8 AM and the race begins at 9:30 AM.

Leashed dogs are welcome in the outdoor Hop Yard area of this festive holiday event! Browse local vendors, take photos of Fido with Santa, gather around the bonfire, and stay for the tree-lighting ceremony.

The Arthritis Foundation’s race is the original festive race for charity with your pup. It’s where you can strut your stuff in your favorite holiday costume. Bring a team of friends, family, and co-workers to run or walk. Please ensure your dog is kept on a leash. Check in starts at 8 AM and the race begins at 9 AM.

The Arthritis Foundation’s race is the original festive race for charity with your pup. It’s where you can strut your stuff in your favorite holiday costume. Bring a team of friends, family, and co-workers to run or walk. Please ensure your dog is kept on a leash. Check-in starts at 9 AM and the race begins at 10 AM.

Book a special 2-night stay on this special weekend to celebrate the holidays with Fido! Enjoy a festive dog-themed getaway featuring group strolls through a historic village, sing-alongs, costume parties with prizes, holiday treats, and professional photos with your pup. The holiday weekend also includes breakfasts where dogs are welcome, a seasonal parade, a pajama party with prizes for matching family outfits, and a guided dog-friendly sculpture tour. All breeds are welcome, and special lodging packages include holiday activities and organic dog treats.

Bring Fido to this fun, annual holiday event! There will be lots of activities, including the Reindog Parade on Saturday at 2 PM, old-fashioned caroling, pop-up shops, a nonprofit fair, and horse-drawn carriage rides! Merchants will be open with specials and restaurants will be ready to serve you up their best holiday cheer.

Bring Fido to meet Santa and the Grinch just in time for holiday photos. Reservations are required.

Bring Fido to the Park Plaza area for this annual celebration of Hanukkah with the Chabad of Yonkers! There will be a traditional menorah lighting ceremony, along with lively family-friendly entertainment, festive activities, and delicious treats. This event is rain or shine.

On select days, bring your pup for a festive photo with Santa! Appointments are recomended as walk-ups will only be taken based on availability.