Dog Events in Sheffield, MA

Here are the pet friendly events closest to Sheffield. Use the links below to get details on each event, print directions, look at pictures, and even read reviews of last year’s event.

Jun 28

Fairfield Dog Days hosted by Pet Pantry Warehouse

Fairfield, CT

Fairfield Dog Days hosted by Pet Pantry Warehouse Get ready for an entertaining event that your pup and the whole family will enjoy. The day will be filled with pet-centric activities, competitions and vendors. The event proceeds will be donated to local animal shelters and rescues, including Adopt-A-Dog, Operation Hope, and Team Woofgang & Co. See Details

Jun 27–28

Annual East Hampton Art Affair

East Hampton, NY

Annual East Hampton Art Affair Leashed dogs are welcome at this annual fair that features local and national artists showcasing a diverse range of fine art, including sculptures, jewelry, woodwork, paintings wearable art and more. Visitors will have the chance to meet artists, explore their techniques, commission custom pieces, and learn about their inspirations. See Details

Jun 28

The Pet House Party: Commack Animal Hospital Grand Opening Celebration

Huntington, NY

The Pet House Party: Commack Animal Hospital Grand Opening Celebration Celebrate the opening of a new veterinary hospital with an afternoon of community fun, including tours, giveaways, a food truck, pet photo opportunities, kids’ activities like stuffed animal “surgery,” and chances to meet the veterinary team. Guests are invited to bring family and pets while learning more about the hospital’s services and enjoying a welcoming, interactive experience for all ages. See Details

Jun 28

4th of July Pet Photo Event

Hawthorne, NJ

4th of July Pet Photo Event Dress your furry friend in their best red, white, and blue attire and strike a pose at this patriotic pet photo event celebrating America's 250th birthday. Participants can enjoy festive photo opportunities, complimentary treats, and a fun-filled day creating memorable snapshots with their four-legged companions. See Details

Jul 25

Botanicals and Brews at Lilac Hedge Farm

Rutland, MA

Botanicals and Brews at Lilac Hedge Farm 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. See Details

Jun 5–Jul 31, except Jul 3

Live Concert Series at Ridge Hill

Yonkers, NY

Live Concert Series at Ridge Hill Enjoy free outdoor concerts every Friday (no show July 3rd) with Fido, featuring live performances from a variety of musical genres in a lively community setting. Guests are encouraged to bring lawn chairs and relax while enjoying an evening of music, food, and drinks from nearby restaurants and on-site beverage vendors. Seating is available on a first-come, first-served basis, and concerts may be canceled in the case of inclement weather. See Details

Jun 3–Aug 12

Dog Crafts at the Bryant Park Art Cart

New York, NY

Dog Crafts at the Bryant Park Art Cart Join the AKC Museum of the Dog each Wednesday from June through August for this fun, dog-themed art series! These free, all-ages workshops feature a new craft each week, with all materials provided and no registration needed. The outdoor space is dog-friendly, so bring your pup along for inspiration. Find the Art Cart on the Upper Terrace near the William Cullen Bryant statue. See Details

Select Apr–Aug 2026

Must Love Dogs - Dog-Friendly Comedy Show East Village

New York, NY

Must Love Dogs - Dog-Friendly Comedy Show East Village Get ready to laugh as your furry friend howls for a night of tail-wagging fun. Enjoy canine-themed jokes and drinks with your pup. This show is recommended for audience members ages 18+ and occurs one Friday each month. Check their website for current schedule. See Details

Aug 15–16

Annual Seafood & Wine Festival at Robibero Winery

New Paltz, NY

Annual Seafood & Wine Festival at Robibero Winery Gather your family and friends for a lively celebration of coastal flavors, fine wine, and sweeping vineyard scenery. This festive outdoor experience features seafood and wine stations, live DJ entertainment, games, activities, and artisan vendors throughout the grounds. Well-behaved dogs are welcome to take part in the day. A portion of the proceeds will be donated to the American Cancer Society. See Details

Aug 22

Dog-Friendly Day Retreat: Tails of Adventure

Simsbury, CT

Dog-Friendly Day Retreat: Tails of Adventure Enjoy a one-of-a-kind wellness retreat designed for both you and your dog, focused on strengthening your bond through shared experiences. The day includes a mix of adventure and relaxation with activities like dog yoga, meditation, training sessions, hiking, paddling, and group swim time. Guests can also take part in workshops, crafts, and educational seminars. See Details

Aug 22–23

Honey Festival at Waterdrinker Family Farm & Garden

Manorville, NY

Honey Festival at Waterdrinker Family Farm & Garden Leashed dogs are welcome at this sweet summer celebration that honors the vital role of bees and pollinators with a weekend full of family-friendly fun. Guests can explore vibrant sunflower fields, enjoy honey-themed photo ops, and learn about pollination through interactive exhibits. The festival also features live music, local vendors offering honey-inspired treats, food trucks, and activities like jumbo jump pads, mini golf, and more. See Details

Sep 5–6

Westhampton Fine Art Festival

Westhampton Beach, NY

Westhampton Fine Art Festival Leashed dogs are welcome at this annual festival that brings together talented artists from across the country to display and sell original, handmade works in a wide range of mediums — including painting, sculpture, glass, ceramics, jewelry, photography, fiber, mixed media, and woodworking. Visitors can explore the open-air gallery, meet the artists, and purchase unique pieces for their home, office, or as gifts. See Details

Sep 12–13

Garlic Festival at Waterdrinker North Fork

Riverhead, NY

Garlic Festival at Waterdrinker North Fork Celebrating the harvest season, this dog-friendly festival features live music, a vendor market with garlic-inspired goods, food trucks, and activities across the 40-acre farm. Attendees can enjoy sunflower fields, pumpkin picking, a corn maze, a garlic scavenger hunt, and a musical hayride. Unique treats like garlic ice cream and garlic butter roasted corn will be available. See Details

Sep 26

Steampunk Day at Old Rhinebeck Aerodrome Air Show

Red Hook, NY

Steampunk Day at Old Rhinebeck Aerodrome Air Show On Steampunk Day at the Old Rhinebeck Aerodrome Air Show, aviation history meets imaginative Victorian‑era science‑fiction fun. In addition to the museum’s usual airshow flying schedule, the themed day includes opportunities to see vintage planes in flight alongside steampunk characters and costumes, and creative activities inspired by steampunk culture. Please note that the airplanes can be very noisy, and there could be an occasional gunshot or explosion. See Details

Sep 24–27

Canine Camp Getaway East Durham

East Durham, NY

Canine Camp Getaway East Durham Enjoy the ultimate dog vacation in the scenic Catskill Mountains! Grab your dog for a unique, all-inclusive vacation with activities ranging from agility, hiking, and pet-friendly pool fun to lure coursing, vet seminars, nose work, disc dog, canine freestyle dance, barn hunt, Therapy Dog training and testing, and so much more! At night, enjoy dog-friendly evening entertainment like country line dancing, movie night and a musical comedy show. No formal training is required; all friendly dogs are welcome. See Details

Oct 3

Dog-Friendly Day Retreat: Paws 'N' Reflect

Simsbury, CT

Dog-Friendly Day Retreat: Paws 'N' Reflect 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. See Details

Sep 26–Oct 4

Grape Stomping Festival at Robibero Winery

New Paltz, NY

Grape Stomping Festival at Robibero Winery Get ready for a lively vineyard celebration featuring grape stomping, live music, lawn games, and cozy bonfires in a scenic outdoor setting. Guests can enjoy wine tastings, sangria, craft beverages, wood-fired pizza, and artisan snacks while relaxing on the lawn. Families and pets are welcome to join the fun, and covered seating is available rain or shine. See Details

Oct 10

DogFest Long Island-Northeast Region

Massapequa Park, NY

DogFest Long Island-Northeast Region 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! See Details

Oct 11

Annual Pets in the Park Danbury

Danbury, CT

Annual Pets in the Park Danbury 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. See Details

Jun 20–Oct 18, weekends only

Old Rhinebeck Aerodrome Air Shows

Red Hook, NY

Old Rhinebeck Aerodrome Air Shows Visitors and leashed dogs are welcome each weekend to watch thrilling flight demonstrations featuring authentic historic aircraft, and enjoy educational exhibits. Bench and bleacher seating are available, and a limited number of camp chair rentals. Concessions are also available for purchase. Please note that the airplanes can be very noisy, and there could be an occasional gunshot or explosion. See Details