My four “grand” pups visit — and sometimes stay — at my home, but I had never traveled with any of them until my youngest daughter, Jen, adopted Penny, a 5-pound Chiweenie who spends much of her time quietly in a pouch, inseparable from her caregiver. So, when Jen proposed traveling together, I applauded her dog-friendly choice just two hours from Manhattan: Woodstock, New York, the artsy Catskills colony where music flourishes.

Woodstock is a small, rural, year-round community for those who appreciate the beauty of nature. They can hike Sloan Gorge Loop or Overlook Mountain or gallery hop by day, and spend evenings grooving at a concert or sitting by the fire. Though second homeowners may be city sophisticates, the town’s shops are decorated with peace signs and sell tie-dye tees and hippy jeans.

© Irvina Lew

Jen discovered Woodstock Way Hotel, which overlooks a woodsy waterfall only footsteps behind Tinker Street, the main drag in the center of town. The complex, which won the 2022 American Institute of Architects Honor Award, integrates into the woods like a contemporary campground; its individual, two-story cabins are made of reclaimed wood and have balconies viewing the woods, stream or Tannery Brook Waterfall.

The construction is both great looking and sustainable. Materials used in its construction leave a low carbon footprint, and the hotel also features living roof systems and bio-retention ponds.

The Tannery, a standalone building at the entry to the property, serves as the dog-friendly communal guest space. It’s an all-purpose lobby, complete with a lounge, art-filled boutique, and breakfast room with a coffee bar and pastries for sale. Outside, an extravagantly sized terrace — with fire pits and Adirondack chairs — is close and directly faces the waterfall, which we could also see through a windowed wall in our suite’s living area.

© Irvina Lew

The room housed a couch, TV, mini fridge and a desk with a record player ready for vinyl records still popular around town. The sleeping corner, with its king-sized bed, was the perfect spot to listen to the waterfall and snuggle with a furry friend. The room was well equipped with drawers, closets and a modern bathroom. The setting enhanced our stay, whether we were in our room or not.

Just a minute’s walk up the hill reaches the shops, cafés and restaurants on and around Tinker Street. One day, while I drove 60 miles to Bethel Woods, Jen — with the puppy — spent much of the day popping in and out of shops on foot.

When I returned, Jen told me, “I found so many shop owners who greeted Penny, it made browsing around more fun. In most places, even coffee shops and restaurants, we were greeted with a biscuit, a bowl of water or just lots of cuddles and curiosity. There were so many others with pets, I spent the entire morning chatting with them about their dog’s breed and traveling habits. There’s even an off-leash dog park that would be perfect for my other dog.”

The next morning, at Bread Alone, I noticed bags on the counter reading Pookies Cookies Dog Treats, and was told a staff member made them for customers’ pets. In fact, some restaurants offer outside seating for dog owners, including Garden Café, which specializes in organic and vegetarian dishes, and Cucina, where a restored farmhouse is the setting for Italian fare and dogs are welcome on the porch.

With holiday events, Woodstock Winter Farm Festival and Winter Markets, Woodstock is surely a hospitable spot. One caveat: Don’t confuse Woodstock with where the Summer of Love took place, that one is 90 minutes away at Bethel Woods!

Woodstock Way Hotel

10 Waterfall Way

Woodstock, NY 12498

tel 845 684 5911