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Dog Events in Winchester, CT

Here are the pet friendly events closest to Winchester. 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 Sip and Paint a Pet Portrait Fun at Barking Dog

Fridays, Jul–Aug

Sip and Paint a Pet Portrait Fun at Barking Dog

Sip and Paint a Pet Portrait Fun at Barking Dog

On select dates, guests can bring Fido and paint a portrait of him! Artist Michele Cahill will help each pet parent masterfully paint their best canine friend. Please note that you must register in advance and email a picture of your dog to Michele prior to attending.

Pet Friendly Dog-Friendly Day Retreat: Tails of Adventure

Aug 22

Dog-Friendly Day Retreat: Tails of Adventure

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.

Aug 22–23

Honey Festival at Waterdrinker Family Farm & Garden

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.

May 2–Aug 29

Patio Party at Bear's Smokehouse BBQ

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!

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.

Sep 5

Keyport's Stars & Stripes Food Truck & Music Festival

Keyport's Stars & Stripes Food Truck & Music Festival

Kick off Memorial Day weekend with Fido and a full day of food, music and family-friendly fun. Guests can sample a wide variety of gourmet food trucks offering everything from savory favorites to sweet treats, while enjoying live performances from local bands throughout the day. The event also features vendors, a beer and cocktail garden for adults, and plenty of activities for kids.

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.

Select , Apr 14–Sep 8

Bark in the Park with Somerset Patriots

Bridgewater, NJ

Bark in the Park with Somerset Patriots

Bring Fido out to the ballgame! All pet owners attending the game with their dog are asked to bring paperwork displaying proof of vaccination and their dog ID tag to be checked before entry outside the main gate. There will be a pre-game Pooch Parade around the warning track of the field, water stations available on concourse, giveaways, dog-related vendors and more for your pup. Every fan that plans on bringing their dog is required to fill out an online waiver in advance. Dogs don't need a separate ticket. Games for 2026 are scheduled for April 14, May 26, August 25 and September 8.

Sep 9

Annual Swim Pool Paw-ty at the Glen Rock Pool

Annual Swim Pool Paw-ty at the Glen Rock Pool

Register Fido for this annual gathering co-hosted by the Glen Rock NJ Dog Park and Glen Rock Parks and Recreation. Different times for sizes of dogs will be available to ensure safety and comfort.

Sep 10

Concert for Canines & Their Companions

Concert for Canines & Their Companions

Enjoy a relaxing day with your dog featuring live music by The Juilliard School. Grab helpful pet health resources, enjoy giveaways and visit the photo booth for a memorable keepsake. Please check the event website for updates in case of inclement weather.

Sep 12

Annual Animal Blessing

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.

Sep 12

Pet Palooza 2K Pup Strut

Pet Palooza 2K Pup Strut

A community dog walk that kicks off Manville’s pet‑friendly Pet Palooza festival with a fun, 2K stroll for dogs and their humans. Expect music, vendors, and family activities, with proceeds benefiting local animal causes.

Sep 13

Sip and Paint a Pet Portrait Fun at d.b.a.

Sip and Paint a Pet Portrait Fun at d.b.a.

Bring Fido and paint a portrait of him! Artist Michele Cahill will help each pet parent masterfully paint their best canine friend. Please note that you must register in advance and email Michele a picture of your dog before attending.

Sep 12–13

Garlic Festival at Waterdrinker North Fork

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.

Sep 13

Pups in the Pool at Spook Rock Swimming Pool

Pups in the Pool at Spook Rock Swimming Pool

Let your pups splash, paddle and play in the pool—just for them! Dogs must be accompanied by someone 18+ and have written proof of rabies vaccination.

Select dates, Mar 29–Sep 19

Bark in the Park with the Worcester Red Sox

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.

Sep 19

Bark in the Park: In Memory of Tyler

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.

Sep 19

Cranford Pooch Plunge at Orange Avenue Pool

Cranford Pooch Plunge at Orange Avenue Pool

Dive into the fun at this annual event for dogs! Fido is welcome to splash around before the pool closes for the season. Register in advance to secure your spot. All dogs must be up-to-date on vaccinations and ready to play nicely with others! Time slots are designated by your dog's weight. There's a limit of one dog per adult handler.

Sep 19

Pet Palooza & Food Truck Festival

Pet Palooza & Food Truck Festival

This festival is packed with activities for both two- and four-legged guests, including live music, a delicious lineup of 15 food vendors, pet adoptions, a pet fashion show, and exciting contests. Kids can enjoy the dedicated Kids Zone while pups tackle the canine agility course or strut their stuff on the runway.

Sep 25

Bark After Dark - Furry Friday at AKC Museum of the Dog

Bark After Dark - Furry Friday at AKC Museum of the Dog

Don't miss the opportunity to explore the AKC Museum of the Dog with your furry companions! Enjoy music, special activities, and playful surprises designed for both people and pups—all set against the backdrop of the Museum’s one-of-a-kind collection. Be sure to secure your tickets early, as these popular events often sell out in advance.

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Winchester, CT, US