Dog Events in Phillipston, MA

Whether you’re a die‑hard fan who knows every line or just someone who loves a good witchy romp, this trivia night promises a wickedly fun atmosphere filled with laughter, friendly competition, and a whole lot of “amok, amok, amok.” It’s the perfect blend of nostalgia and Halloween‑season magic—no black flame candle required.

The pet parade will feature fun, costumes and contest with prizes! Parade participants should register online in advance. You only need to register once if you're entering multiple pets as one group costume. If you're bringing multiple pets with different outfits, please register separately.

Enjoy a family-friendly celebration for pets and animal lovers featuring shopping, demonstrations, rescue groups, adoptions, and plenty of activities for both people and their furry companions. Guests can bring their leashed pets to participate in a lively pet costume contest, enjoy an animal blessing ceremony, browse local vendors, and grab food and treats throughout the day. The event also includes face painting and community activities, with a portion of admission proceeds benefiting local animal shelters.

Enjoy a day of art, music, and family fun at this annual festival featuring fine artists, craftspeople, specialty foods, and kid-friendly activities. Leashed dogs are welcome to join.

Grab your sneakers and Fido's leash, and head to the course to support a great cause. They encourage you to get in the spirit and wear your favorite Halloween costume. T-shirts are guaranteed if you register by September 14th.

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.

Celebrate Halloween with your pup at this annual fundraising race! Participants can run or walk the course with their four-legged friends while enjoying a festive day featuring costumes, activities, and plenty of Halloween fun.

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.

Kick back, relax and enjoy some fresh air while you cruise around the harbor taking in all the sights and rich history with your four legged friend. This Halloween-themed cruise lets you dance to your favorite tunes while enjoying the ocean breeze, with complimentary dog treats for your pup and a cash bar with light snacks for humans. Dress up your four-legged companion in a festive costume!

Held in The Liberty Yard, this weekly event features cocktails, frozen drinks, dog-friendly experiences, and community partnerships supporting animal welfare organizations throughout the summer. Bring your pup or meet friends on the patio for a summer afternoon benefiting pets in need! Make a night of it and book a dog-friendly room on site at The Liberty Hotel!

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.

The Laconia Pumpkin Festival, formerly the New Hampshire Pumpkin Festival, welcomes leashed pups to celebrate the season! Expect thousands of glowing carved pumpkins, including the iconic pumpkin tower, live music (plus laser shows and dancing witches), festive parades for kids and costumed pets, artisan and food vendors, the Pumpkin Express train, games like corn-hole and craft stations, and a beer garden.

This dog-friendly Halloween costume parade features a POOCHAPALOOZA zone, photo booth, face painting, free treats and plenty of festive fun. Dogs and their people can compete for grand prizes in categories including Best Costume, Cutest Costume, Scariest Costume, Best Dog and Human Duo, and Best Dog and Child Duo.

This dog-centric Oktoberfest celebration features tastings from local breweries, traditional German fare from food trucks, live music, games, raffles, and more! Taster and Designated Driver tickets are available. This is a 21+ only event and pups must be leashed at all times.

Dress your pup in a Halloween costume for a chance for prizes! Categories will include Best Family Costume, Small Dogs, Big Dogs, Owner/Pair Costume. Guests will also enjoy pet-friendly vendors, a costume parade, 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).

Enjoy Trunk-or-Treat for dogs, decorate Halloween dog cookies ($5, benefiting Long Journey Animal Rescue), free doggie mocktails, a pet costume contest and dog/owner games with prizes, and a spooky pet photo fundraiser. Refreshments, mini trick-or-treat bags, and special event discounts make this a festive, family- and pet-friendly celebration. All dogs must be leashed and vaccinated.

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.

This weekly Yappy Hour invites guests to bring their pups to the outdoor beer garden for an evening of craft beer, outdoor relaxation and pup cups for four-legged visitors. Held every Thursday night, it’s a chance for dogs and their people to enjoy a casual evening together.