Dog Events in Holland, MA

Cruise around the harbor taking in sights and rich history with Fido! You will enjoy views of the city, fish pier, Logan Airport and the USS Constitution to name a few. All dogs must be on a leash at all times. One dog for each paying adult. A cash bar and light snacks will be available for purchase. Dates for 2026 are: May 17th, June 28th, July 26th, August 9th and 23rd, September 6th and 20th.

You and Fido are invited to this annual event which will include a doggie lure course, demonstrations, doggie Olympics, silent auction and raffles! There'll also be live music, vendors, food trucks, and a beer & wine tent! Please note that retractable leashes aren't permitted at the fairgrounds.

Run or walk this peaceful (but fun!) 5K through the beautiful Mine Falls for a good cause. Operation Delta Dog rescues dogs and trains them to be service dogs for veterans - all at no cost to our veterans! This is one of the few 5K events in the area that welcomes you to run with your four-legged leashed running partner. There will be prizes waiting for all dog finishers, as well as special awards for best dressed pups, matching outfits with their human runners, fastest human/dog team and more.

Indulge in an event with popular food trucks serving mouthwatering treats like flavorful hot dogs, delectable lobster rolls and irresistible sundaes. Bring your leashed furry friend to enjoy the delicious fan favorites while basking in the vibrant atmosphere. There will even be a food truck just for dogs!

Explore 70+ juried booths with your leashed pup at this annual event! You'll find handmade goods like sea glass jewelry, nautical décor and gourmet treats. Enjoy specialty foods including kettle corn and infused oils. The event is rain or shine!

Celebrate Oktoberfest with your pup at this dog-friendly event featuring festive beer and cocktail specials, German-inspired food, live music, fun competitions, and off-leash play. Enjoy a stein holding contest, dog holding competition, pup cup eating contest, commemorative beer steins while supplies last, dog treats, pretzel necklaces, and plenty of fall fun for both two- and four-legged guests.

Join Golden Dog Adventure Co at this unique dog-friendly cruise that offers a memorable experience on the water! Guests can relax on a private boat while taking in coastal views, enjoying fresh air, and connecting with a community of dog lovers. The event often features themed elements, lighthearted activities, and opportunities for dogs to mingle. With food and drinks available onboard and plenty of space to unwind, it’s a fun and engaging way to celebrate together in a one-of-a-kind setting.

Join a community 5K supporting local organizations focused on recovery and education. Participants of all fitness levels can walk, run, or jog while enjoying a fun, family-friendly event featuring a Kids’ Fun Run and opportunities for businesses and community members to get involved. Leashed pets are welcome to join the challenge.

Leashed dogs are welcome with you to explore one of Newport's historic neighborhoods during this guided walking tour featuring stories of the people, places, and preservation efforts that shaped the area. Discover how Newport's architecture, craftsmanship, and historic homes reflect the city's journey from the Revolutionary era to modern-day resiliency. The tour takes place rain or shine, and includes walking over uneven sidewalks. Please note that dogs aren't permitted inside any buildings.

Bring Fido to the expo, which is part of the Long Island Family Festival! The day will feature a lure course, exciting demonstrations, pet-focused vendors, and local rescue and adoption groups. Don’t forget to dress up your furry friend for the costume contest!

Dog lovers and their pups are invited to enjoy a community fundraiser benefiting Pet Peace of Mind, a program that helps hospice patients care for their beloved pets. The event features enrichment activities, opportunities to connect with fellow dog owners, and information about the important support the program provides to families and their animals.

Experience a wellness-focused retreat designed for you and your dog, centered on strengthening your bond through shared activities and relaxation. The experience includes a mix of adventure and enrichment like dog yoga, meditation, training, hiking, paddling, and group swim time, along with creative workshops and educational seminars.

This dog-friendly festival raises funds for the local animal shelter while helping adoptable animals find loving homes. Guests can browse vendors, enter raffles and enjoy free pup cups and frisbees, along with a K9 demonstration and a festive costume parade.

A charity 5K run/walk that welcomes runners, walkers, and their dogs to Hopkinton State Park to raise funds for the Baypath Humane Society. The event features a Doggie Division for participants running or walking with their dogs, vendor village, and community activities supporting animals in need.

Bring Fido for a fun afternoon of live music, vendors, food, contests, and more than 150 animal organizations broadcasting their causes. Attendees can meet adoptable pets, learn from educational exhibits, and connect with animal welfare groups working to protect and support animals. The event also hosts contests, demonstrations, and interactive activities to engage both pets and their owners.

Gather your friends, family and dog to join the fun in celebrating the human-canine bond. Everyone is invited for a day of fun and festivities. Activities include inspiring speakers, dog demonstrations, agility courses, and the annual costume contest!

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.

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.