Dog Events in Chester, CT

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 to capture a photo with Santa! The jolly man will be inside ready to meet your pup.

This dog-friendly Friendsgiving celebration features a Turkey Trot costume contest, a pup-kin pie lick-off, gift bingo, professional fall photos and a special Dogsgiving menu for pups. Guests can also enjoy live music, food, drinks, curated vendors and a dog-friendly patio while supporting Paws of War through raffle baskets and a 50/50 drawing.

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.

This dog-friendly holiday market features local vendors (many that are dog friendly!) selling gifts and seasonal goodies. Guests can bring their pups while shopping, enjoying festive treats, and sipping mulled wine and seasonal cocktails.

Leashed pups are welcome at this festive outdoor market! There will be free raffles to enter, food trucks, holiday music, local vendors and so much more. Well-behaved and leashed pups are welcome.

Leashed dogs are welcome at Franklin Park Coalition’s annual race - the largest Thanksgiving Day race in the city of Boston. There will be awards for the fastest racers, including the fastest dog, and awards for costumes!

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 your furry friends, big or small, and watch them strike adorable poses with Santa! Pet Photos will be located on the Lower Level, near Dick's Sporting Goods. Photos will be taken and available for purchase at this event. Reservations are recommended but not required.

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 starts at 9:00 AM and the race begins at 10:30 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.

This dog-friendly holiday event invites guests to bring their pups for photos with Santa in a festive Whoville setting! Visitors can enjoy seasonal treats, holiday cocktails, and Christmas cheer while capturing a holiday photo with their furry friends. Photos are donation-based and available on a first-come, first-served basis.

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.

On select Sundays, bring your furry friends, big or small, and watch them strike adorable poses with Santa! Pet Photos will be located on the Lower Level near Lululemon. Photos will be taken and available for purchase at this event. Make your reservation to see Santa online.

Bring your furry friends, big or small, and watch them strike adorable poses with Santa! Pet Photos will be located in the JCPenney Court on Level 1. Photos will be taken and available for purchase at this event. Reservations are recommended but not required. The event will be held on November 22nd and December 6th.

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.