Here are the pet friendly events closest to Cumberland. Use the links below to get details on each event, print directions, look at pictures, and even read reviews of last year’s event.
Bark in the Park with the Worcester Red Sox
Bring your furry friend for a day of fun and baseball! Dog-friendly days for 2025 include March 30, May 4, July 20, and August 3. There will be a pregame doggie parade, vendors with cool giveaways, and much more! Your ticket includes admission for you and your pup, plus a WooSox branded dog item.
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Alpha Dog Bark Market
Held on the last Sunday of each month from April through October, pups can enjoy a Fun Run Corral, on-site dog park, and more, while their humans can relax with food, acoustic music, beach volleyball, horseshoes, bocce, and cornhole toss. Plus, a variety of vendors will be offering unique products and services for both dogs and their owners. Local rescue and shelter partners will be on site to raise funds, provide education, and connect with potential fosters and adopters. Pre-register on the event page, complete the Fun Run waiver, and you'll receive a free Barkwell Dog Treat and a raffle entry!
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First Friday in Downtown Concord
Leashed dogs are welcome the first Friday of every month from May through November when businesses are encouraged to stay open late and the streets come alive with food trucks, live performances, art displays and other activities.
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Dog Days of Summer Boston Harbor Cruise
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 2025 are: May 17th, June 1st and 21st, July 12th and 27th, August 16th and 31st, September 13th and 28th.
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Ulti-Mutt Dog Day
On May 18th, July 27th, and September 28th, enjoy a day of fun featuring local dog-friendly vendors, tasty eats from a food truck, and the highlight of the event - an exciting lure course! Whether it’s your dog’s first run or their tenth, the course is all about having fun (not competition), so no points - just paws and play! Please note: This event is weather-dependent and may be canceled in the case of inclement weather for everyone’s safety.
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Newburyport Dog Bash
This lively, dog-friendly celebration invites you and Fido for a fun-filled afternoon featuring craft beer, delicious food, live music, local vendors and classic yard games. Families are welcome, with free activities like coloring, temporary tattoos and more.
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Annual Barbecue Fundraiser
Bring Fido to this annual event that supports rescue dogs! Your ticket includes a mouthwatering BBQ buffet by Firefly BBQ, dessert and a chance to win an Apple iPad raffle. Enjoy a fun afternoon filled with a silent auction, sales booths, cash bar and great company with fellow dog lovers. The event takes place under a covered pavilion, rain or shine, and all dogs are welcome!
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Ulti-Mutt Dog Day
On June 22nd and August 10th, enjoy a day of fun featuring local dog-friendly vendors, tasty eats from a food truck, and the highlight of the event - an exciting lure course! Whether it’s your dog’s first run or their tenth, the course is all about having fun (not competition), so no points - just paws and play! Please note: This event is weather-dependent and may be canceled in the case of inclement weather for everyone’s safety.
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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. The festival hours are Friday from 12 PM until 6 PM, Saturday from 10 AM until 6 PM, and Sunday from 10 AM until 5 PM.
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Liberty Weekend Craft Festival
Celebrate Independence Day with your leashed pup at this outdoor event featuring over 75 juried artisans showcasing handmade crafts, including quilted accessories, glass lanterns, woven baskets and more. Enjoy live music, savor delicious treats like artisanal sourdough and authentic cannoli.
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Summer Artisan Festival at Lilac Hedge Farm
Celebrate summer at this fun festival with Fido! With over 60 vendors to explore, it's the perfect weekend to shop, support local artisans and treat a special mom in your life. Enjoy live music throughout the day, with afternoon performances from 1-4 PM and an evening show from 5-8 PM. Savor delicious eats from the Farm Kitchen & Bar, along with tasty offerings from visiting food trucks. Stop by the farm stand on your way out for fresh local goods and treats. An on-site ice cream stand provides a sweet treat for guests and pup cups for Fido. While dogs aren't permitted near the resident farm animals, they're welcome to join their owners at picnic tables and other designated outdoor spaces.
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Chatham Liberty Arts & Craft Festival
Bring Fido along as you explore 55 juried artisans offering handmade goods like sea glass jewelry, resin art and nautical décor. Enjoy specialty foods including kettle corn, infused oils and maple syrup. The event is rain or shine.
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Cape Cod Dog Center Fest
The day will be packed full of dog-friendly activities and entertainment! Enjoy a variety of interactive experiences such as a doggie pool party, pup cup ice cream station benefiting rescue dogs, dog contests with prizes, music by Cape Tunes DJ, and more.
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Pup Crawl - Humane Society for Greater Nashua
Bring your pups and support local breweries and the Humane Society for Greater Nashua. The kickoff party will be at Kettlehead on Main in Nashua with the finale event at the Anheuser-Busch Biergarten in Merrimack. You must be 21+ to purchase tickets.
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Sandwich Summer Craft Festival
Explore over 75 juried artisans showcasing handmade crafts like sea glass jewelry, coastal art, and gourmet treats with your leashed pup! Guests can also enjoy specialty foods including kettle corn and infused oils. The event is rain or shine.
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Brewster Summer Arts & Craft Festival
Shop with your leashed pup and explore over 100 juried booths featuring handmade crafts, coastal art and specialty foods. Enjoy live music and scenic views along historic Route 6A. The event is rain or shine.
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Woofstock Festival
Bring Fido out for a groovy afternoon of fun for the whole family - rain or shine! The event will feature live music, food trucks, local craft brews and lots of doggone fun. There’s something for everyone including games, kids activities, a bounce house, dog agility courses, makers and craft vendors, giveaways, and so much more! This event raises funds to support the health and wellbeing of both resident (shelter) pets and pets of local community members who utilize AWS’ Community Veterinary Clinic in Kennebunk, ME.
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Chatham Summer Craft Festival
Explore 55 juried artisans offering handmade goods like sea glass jewelry, resin art, and gourmet treats with your leashed dog! Enjoy specialty foods including infused olive oils and chocolate chip cannoli. The event is rain or shine.
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Dog Day at the Ashland Farmers Market
Bring your four-legged friend to the market and check out fun activities at the special dog vendors! All dogs must be crowd friendly, leashed and well behaved.
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Nauset Summer Craft Festival
Bring Fido shopping at over 100 juried booths featuring American-made arts, crafts, and specialty foods, including sea glass jewelry, nautical décor and gourmet treats. Enjoy live music and scenic views along historic Route 6A. The event is rain or shine!
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