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Dog-Friendly Activities in Old Chatham, NY

There are 57 dog-friendly activities within 40 kilometers of Old Chatham. Use the links below to get an overview of each one, see pictures, print directions, and even read reviews from other dog owners. Coming from out of town? Get a discounted rate on pet friendly hotels in Old Chatham.

Pet Friendly Hilltop Orchards

Hilltop Orchards

Hilltop Orchards

Leashed pups are allowed to join you at Hilltop Orchards, a pet-friendly, family-run orchard, cidery and winery in Richmond, MA. Home to 16 acres of prime apple trees, you can enjoy apple cider, artisanal craft ciders, wine tastings and incredible apple cider donuts made fresh daily. Then, explore the hiking trails throughout the property that offer excellent Berkshire views.

Pet Friendly Norman Rockwell Museum

Norman Rockwell Museum

Stockbridge, MA

Norman Rockwell Museum

Leashed dogs are welcome to join you as you explore the pet-friendly grounds of the Norman Rockwell Museum in Stockbridge, MA. The museum houses the world’s largest and most significant collection of Rockwell’s work. While Fido can not browse the artwork inside, the grounds offer 36 acres to explore, including sculptures, lovely landscaping, scenic views and picnic tables. Note that pets may not be left unattended in cars or anywhere else for owners to enter the museum.

Balderdash Cellars

Balderdash Cellars

Fido is welcome to join you inside or at an outdoor table at Balderdash Cellars, a pet-friendly winery in Richmond, MA. Enjoy a variety of wine options including white, red and rosé, which you can buy by the glass or try multiple by doing a tasting. You are welcome to bring your own food.

TurnPark Art Space

West Stockbridge, MA

TurnPark Art Space

TurnPark Art Space in West Stockbridge, MA, invites leashed dogs to join you as you view a variety of contemporary architecture and sculptures. The former marble quarry features 16 acres of land with a diverse topography, including hills, meadows, and a lake. The park consists of two levels. The lower level is paved with marble chip and limestone and the upper level retains its natural appearance.

The Mount, Edith Wharton's Home

The Mount, Edith Wharton's Home

The Mount, Edith Wharton's Home, is a dog-friendly venue in Lenox, MA. The famous novelist loved dogs, and as such, Fido is welcome to join you on the grounds as long as they remain leashed. Visit and see the home that Edith Wharton designed herself, right down to the sunken Italian garden.

Art Omi

Art Omi is a pet-friendly, not-for-profit arts center with a 120-acre facility in Ghent, NY. Fido is welcome to tag along to explore the grounds and sculptures but must register for their dog pass program in the visitor center. Your furry friend can be off-leash in the architecture fields from October 1 until April 30 before 8:30 AM on weekdays.

Hudson Ferry Co.

Hudson Ferry Co.

Hudson Ferry Co. is a pet-friendly attraction in New York. Well-behaved dogs are welcome to hop aboard to take their daily commute between Hudson and Athens or join their one-hour sightseeing cruise throughout the day. You'll come across the Athens Hudson Lighthouse, under the Rip Van Winkle Bridge, and back to the Henry Hudson Riverfront Park, where you boarded. Snacks and drinks are also available for purchase.

Dutch Apple Cruises & Tours

Dutch Apple Cruises & Tours

Dutch Apple Cruises offers scenic, dog-friendly boat tours along the Hudson River in Albany, NY, showcasing the region's natural beauty and historic landmarks. With a variety of cruise options available, including sightseeing tours, dinner cruises, and private charters, visitors can enjoy a unique perspective of the area's landscape and attractions. The company's vessels feature spacious decks, onboard amenities, and knowledgeable guides, providing an immersive and enjoyable experience for two-legged and four-legged guests. Also, be sure to check their event page for special dog-focused cruises!

Forged Brewing Co.

Forged Brewing Co.

Forged Brewing Co. in Bainbridge, NY, is a charming brewery and winery nestled in the woods of Coventry. Enjoy a relaxing atmosphere, flavorful beers and tasty wines. Well-behaved, leashed dogs are welcome at the pet-friendly outdoor seating area.

Olde English Downtown Dog Park

Olde English Downtown Dog Park

Local and visiting dogs alike will feel right at home inside Albany's Olde English Downtown Dog Park. This grassy, urban space in New York offers Fidos of all sizes a fenced area to run and play off leash. Amenities include waste bags, benches, and large rocks where pooches can climb, as well as a beautiful mural featuring some of Albany's best four-legged friends.

Pittsfield State Forest

Pittsfield State Forest

Leashed dogs are welcome at Pittsfield State Forest, a pet-friendly natural area in Pittsfield, MA.There are 30 miles of trails to explore at this huge, 11,000-acre park, including the Taconic Crest Trail and the Tranquility. Berry Pond is also a popular spot in the park that offers swimming and fishing opportunities.

Olana State Historic Site

Olana State Historic Site

Olana State Historic Site is a historic house museum and property in Greenport, New York, near the city of Hudson. The estate was home to Frederic Edwin Church, one of the major figures in the Hudson River School of landscape painting. Access to Olana’s dog-friendly, 250-acre landscape is free. The park is open every day from 8 AM to sunset. Bring Fido to explore Frederic Church’s designed landscape with five miles of carriage roads as a way to enjoy the outdoors.

Pittsfield Dog Park

Pittsfield Dog Park

Fido is sure to enjoy a day spent with friends at Pittsfield Dog Park, located in Pittsfield, MA. The dog park is a fully-fenced in, off leash area with separate spaces for large and small dogs. Well-behaved dogs are welcomed to exercise and socialize in a clean, safe environment. A hydration station will provide relief for thirsty pets at play! Dogs visiting Pittsfield Dog Park must be at least six months old and be licensed, vaccinated and spayed or neutered. All dogs should be wearing their tags and remain within view of their owners. The dog park is open from dawn until dusk.

Martin Van Buren National Historic Site

Martin Van Buren National Historic Site

Martin Van Buren National Historic Site is a pet-friendly attraction in Kinderhook, NY. Tour the grounds surrounding the eighth president's house with your leashed pooch. Don't forget to clean up any mess left behind and to respect other visitors. Martin Van Buren National Historic Site is open every day of the week from 9:00 AM to 4:30 PM.

Scenic Hudson’s Long View Park

Scenic Hudson’s Long View Park

Walk your leashed dog at Scenic Hudson's Long View Park. The first thing that greets you upon entering the park is an old red barn, which attests to the land’s centuries-long incarnation as a farm. The park is open daily from dawn to dusk.

French Park Dog Park

Great Barrington, MA

French Park Dog Park

Fido can play off-leash at French Park Dog Park in Great Barrington, MA. This fenced dog park features two spacious, grassy areas and waste stations. Please bring water for Fido, and register on their website prior to enjoying the dog park.

Les Trois Emme Winery and Vineyard

New Marlborough, MA

Les Trois Emme Winery and Vineyard

Fido can join you in outdoor spaces at Les Trois Emme Winery and Vineyard in New Marlborough, MA. This family-owned, dog-friendly winery offers wine tastings and lovely vineyard views. You and your leashed pup are welcome to explore the grounds. Please be sure to call the winery during inclement weather to confirm they are open prior to visiting.

Colonie Center

Colonie Center is a pet-friendly shopping district in Albany, NY. This mall has retail stores, restaurants and other services that may allow you and your pup to join them! Many shops have signs on their windows stating whether or not your furry friend is allowed in, but it's up to pet owners to inquire about dog policies before entering. Please note that dogs must be leashed (6' max) and aren't permitted on escalators or elevators, or in the Food Court or the Play Park. Cleanup materials are located at designated DogComfort Stations within the Center’s common areas.

Jericho Drive-In

Jericho Drive-In

Four-legged friends are invited to spend an evening under the stars with their owners at the Jericho Drive-In in Glenmont, NY. This pet-friendly attraction invites customers to visit them seasonally for a nostalgic night, watching a movie and chowing down on delicious bites from the walk-up concession stand. Dogs must be leashed outside your vehicle and remain quiet during the movie.

Department of General Services Dog Park

Department of General Services Dog Park

Fido is invited to play at the Department of General Services Dog Park in Albany, NY.The fenced-in area sits just north of Huck Finns Warehouse and the I-90 bridge overpass. Dogs must be sociable, current on all vaccinations and under their owner's control at all times.

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Old Chatham, NY, US