Rating:

    Dog Events in Bolton, CT

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

    Pet Friendly Honey Festival at Waterdrinker Family Farm & Garden
    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
    Pet Friendly Dogs in the Drive-Thru at Chick-fil-A North Haven
    Aug 25

    Dogs in the Drive-Thru at Chick-fil-A North Haven

    North Haven, CT
    Dogs in the Drive-Thru at Chick-fil-A North Haven Dogs who visit the drive-thru with their family will receive a treat and fun surprise, while supplies last! See Details
    Aug 26

    National Dog Day = Free Pup Cups at Eastern Edge Food Hall

    Cambridge, MA
    National Dog Day = Free Pup Cups at Eastern Edge Food Hall Celebrate National Dog Day with your pup and enjoy a free pup cup at the pickup window of Cafe Bacaro's. Bring your furry friend along for a special treat and a cool way to celebrate together. The offer is available in person while supplies last. See Details
    Aug 29

    Framingham Food Truck & Craft Beverage Festival at Eastleigh Farm

    Framingham, MA
    Framingham Food Truck & Craft Beverage Festival at Eastleigh Farm Leashed dogs are welcome at this outdoor festival that features a rotating lineup of food trucks serving diverse cuisine, craft beverage options, live entertainment, lawn games and local artisan vendors. It’s designed as a family-friendly celebration where friends and neighbors can enjoy great food and summer atmosphere together. See Details
    May 2–Aug 29

    Patio Party at Bear's Smokehouse BBQ

    New Haven, CT
    Patio Party at Bear's Smokehouse BBQ Spend the weekend enjoying live music (2 PM - 6 PM), barbecue, and outdoor fun at this family-friendly patio gathering. Guests can relax with happy hour specials, yard games, and great food while soaking up the atmosphere with their leashed pup! See Details
    Aug 29

    Neighborhood Walk: 1776|2026

    Newport, RI
    Neighborhood Walk: 1776|2026 Leashed dogs are welcome with you to explore one of Newport's historic neighborhoods during this guided walking tour highlighting stories of the people and places connected to the American Revolution. Guests will discover historic homes, learn about restoration efforts ahead of the nation’s Bicentennial, and see how Newport Restoration Foundation continues preserving these important sites. The tour takes place rain or shine, and includes walking over uneven sidewalks. Please note that dogs aren't permitted inside any buildings. See Details
    Aug 29

    Groveland Dog Bash

    Groveland, MA
    Groveland Dog Bash Bring your pup out for a fun afternoon of live music, food, and yard games! Families are welcome to enjoy activities for kids while browsing vendors, including Skin Charge, That Dirty Dog Soda Pup, and more. See Details
    Aug 29–30

    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
    Aug 30

    Queer and Trans Hiking Fell-ows

    Medford, MA
    Queer and Trans Hiking Fell-ows Leashed dogs are welcome to join this hike through rocky trails with some elevation changes. The 3- to 4-mile moderate hike offers an opportunity to explore the outdoors while meeting new friends in the LGBTQIA+ community. Participants should bring sturdy footwear, water, snacks, and layers as needed, and be prepared for muddy conditions. See Details
    Sep 5

    Pride in Our Pups

    Medford, MA
    Pride in Our Pups A day to connect with LGBT dog owners and allies! There will be vendors, a family-friendly drag show, lawn games 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

    Annual Animal Blessing

    Redding, CT
    Annual Animal Blessing Bring your pet out for an afternoon of walking on the beautiful property while visiting with other animal lovers and their pets. Join in family activities followed by a traditional animal blessing and special guest speakers. The blessing will take place from 12:00–1:00 PM. See Details
    Sep 12

    Autumn Market at Park-9 Dog Bar

    Everett, MA
    Autumn Market at Park-9 Dog Bar Spend a fall afternoon at this dog-friendly community event featuring local vendors, live music, food, drinks, and off-leash play for pups. Shop dog-focused businesses offering handmade treats, pet apparel, portraits, candles, accessories, and more, while meeting local rescue organizations, community partners, and adoptable dogs. Free dog admission is included during the event! See Details
    Sep 12

    Oak & Iron Presents: OAKTOBERFEST

    Andover, MA
    Oak & Iron Presents: OAKTOBERFEST Bring your leashed dog along to enjoy this family-friendly celebration featuring German-style food, live music, games, contests, and plenty of beer. Pets are welcome in the outdoor event areas, while only service animals are permitted inside the brewery. The day also includes pumpkin painting, mini golf, trivia, and other activities for the whole family. 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
    Select dates, Mar 29–Sep 19

    Bark in the Park with the Worcester Red Sox

    Worcester, MA
    Bark in the Park with the Worcester Red Sox On select dates throughout the season, bring your furry friend for a day of fun and baseball! Check their website for full schedule and dog-friendly game days. See Details
    Sep 19

    Bark in the Park: In Memory of Tyler

    Bethel, CT
    Bark in the Park: In Memory of Tyler This special event will be held in memory of the dog park founder's dog, Tyler. It'll be a great way to celebrate his legacy and impact while Fido enjoys the park with other pups and enjoys pup cups from their dog menu. The event will also have pet-focused vendors, food trucks, raffles, live music, demonstrations and more. See Details
    Sep 19

    Haverhill's Woofstock

    Haverhill, MA
    Haverhill's Woofstock Celebrate community, connection, and canine joy at this dog-focused festival featuring adoptable pets, local vendors, live music, food, and interactive activities for dogs and their owners. Guests can enjoy apple picking, pet demonstrations, shopping, and a festive costume contest while learning about fostering and supporting animal rescue efforts. The rain date is September 20th. See Details
    Sep 19

    Tales, Tails & Ales

    Bolton, MA
    Tales, Tails & Ales Bring your well-behaved dog along for a fall afternoon in the orchard featuring craft beer tastings, live author readings, artisan vendors, local food, and live acoustic music. Dogs can enjoy gourmet treats and pet-focused vendors while guests explore local breweries and makers in a scenic New England farm setting. See Details
    May 17–Sep 20

    Dog Days of Summer Boston Harbor Cruise

    Boston, MA
    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 2026 are: May 17th, June 28th, July 26th, August 9th and 23rd, September 6th and 20th. See Details
    Bolton, CT, US