Dog Events in Westbrook, CT

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.

Two- and four-legged friends are invited to attend monthly meetings at the dog park to bring community members together to coordinate volunteers, discuss park updates, and socialize with dogs.

On select dates, guests can bring Fido and paint a portrait of him! Artist Michele Cahill will help each pet parent masterfully paint their best canine friend. Please note that you must register in advance and email a picture of your dog to Michele prior to attending.

Bring your pup to meet Bluey, Skye and Chase! Enjoy local vendors, fun activities, a photo wall and giveaways, plus a chance to meet adoptable dogs from Hotel for Homeless Dogs. Leashed, well-behaved dogs are welcome to join the fun.

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.

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.