Dog Events in Canaan, NY

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

Jul 11

Road Less Traveled Music Fest

Stratford, CT

Road Less Traveled Music Fest Leashed dogs are welcome at this high-energy event features a packed lineup of live bands bringing their signature folk-punk and gypsy rock to the stage. Enjoy craft brews, yard games, a local vendor market and more. Guests are encouraged to bring lawn chairs and blankets. See Details

Jul 5–12

Hop Yard Concert Series

Stratford, CT

Hop Yard Concert Series On Sundays, enjoy a free outdoor concerts with Fido featuring live performances by local and regional bands. Guests can bring lawn chairs, spread out on the grass, and enjoy craft beer, food, and music spanning a variety of genres. Music is weather pending. See Details

Jul 25

Christmas in July Summer Market

Stratford, CT

Christmas in July Summer Market Bring Fido along to this festive summer twist on the holidays with a community market featuring live music, seasonal shopping, and family-friendly entertainment. Guests can browse more than 30 local vendors offering handmade goods, artisan products, gifts, and unique seasonal items while enjoying live performances. See Details

Jul 26

Cruise-In Car Show

Stratford, CT

Cruise-In Car Show Stroll with Fido through an impressive lineup of classic and custom cars, enjoy drinks from the bar, and live music in the yard. Awards will be presented in various categories. 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

Aug 16

Wine & Wags at Aquila's Nest Vineyards

Newtown, CT

Wine & Wags at Aquila's Nest Vineyards Two- and four-legged friends are invited to attend this event, which features adoptable dogs, delicious wine and socializing with friends! Guests can learn about adoption and fostering opportunities, make donations to the rescue, and enjoy time with fellow animal lovers. A minimum beverage purchase is required for each participant, with both alcoholic and non-alcoholic options available. 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

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 29–30

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

Jul 4–Sep 5

Cooler in the Mountains Summer Concert Series

Killington, VT

Cooler in the Mountains Summer Concert Series Enjoy outdoor concerts each Saturday at the resort with top local and national acts! Bring a lawn chair, beach blanket, friends and Fido for a relaxing mountain afternoon. The Snowshed Umbrella bar serves craft Vermont beer, cocktails and snacks during the show, weather permitting. While leashed dogs are welcome, keep them under control and away from concrete areas, as they aren't permitted on the umbrella bar deck. 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 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

Aug 8–9 & Oct 10–11

Annual Summer and Fall Art in the Park

Rutland, VT

Annual Summer and Fall Art in the Park Enjoy a day of art, music, and family fun at this annual festival featuring fine artists, craftspeople, specialty foods, and kid-friendly activities. Leashed dogs are welcome to join. 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

May 16–Oct 25

Hop Yard Concerts

Stratford, CT

Hop Yard Concerts Every Saturday and Sunday from May through October, leashed dogs are welcome at these live outdoor performances from talented local and regional bands across a variety of genres. Enjoy cold beer and savor delicious food. Guests are encouraged to bring lawn chairs and blankets. Start and end times vary by date; see their website for schedule. See Details