One Amazing Day Trip from NYC: Kingston & Woodstock, Upstate, NY (Dog-Friendly)
View from the Ashokan Rail Trail’s Woodstock Dike Trailhead in Woodstock, NY
If you’re craving a day away from New York City, without leaving your furry friend behind, this dog-friendly trip to Kingston and Woodstock in Upstate New York is a quiet escape that will restore you and your four-legged best friend. Just two to two-and-a-half hours north of the city, the trip is easy and scenic, whether you’re driving along the Hudson or taking the Metro-North train from Grand Central Station to Kingston. This day trip encompasses a slow morning of coffee and book browsing, wandering local shops, a scenic stroll with your pup, good food, and soaking in the creative energy of Kingston and Woodstock. It’s the kind of day that might just tempt you to stay overnight, so I’ve included a few ideas for where to rest and keep the adventure going :)
“The journey of life is sweeter when traveled with a dog.”
Start the Day in Uptown Kingston, NY
A SLOW MORNING OF Coffee and Books at Rough Draft BAR & BOOKS
Start your day trip with a stop at Rough Draft Bar & Books, a dog-friendly spot with a calm and welcoming atmosphere. Grab a coffee, and stay a while as you browse their curated collection of books. Get there early to find a peaceful spot with your pup before it fills up.
ExplorE the COLORFUL AND HISTORIC STOCKADE DISTRICT
After coffee, wander the charming streets of Kingston’s Stockade District, where you’ll find historic buildings and boutiques lining an eight-block area. Be sure to stroll down Wall Street to the rainbow crosswalk at John Street, a colorful spot that celebrates the local LGBTQ+ community of Hudson Valley. There’s so much to explore in such a small area. Exit Nineteen was a favorite shop of mine, full of unique little treasures.
Spend the Afternoon in Woodstock, NY
TAKE A Scenic Walk at ASHOKAN RAIL TRAIL’S Woodstock Dike Trailhead
Just a short 15-minute drive from Kingston, the Ashokan Rail Trail is one of the most beautiful spots in the Catskills. The Woodstock Dike Trailhead has wide, scenic paths with views of the mountains and the reservoir along the way. It’s an easy, dog-friendly walk - perfect for stretching your legs (and paws), taking photos, and breathing in fresh Hudson Valley air.
Lunch at ShelteR WOODSTOCK’S Outside Patio
After your walk, you’ll be ready for lunch. Head over to Shelter Woodstock, which has a dog-friendly patio where everyone can unwind. We had some of the best burgers and cold beers, while soaking up the laid-back Woodstock scene.
TAKE AN AFTERNOON STROLL IN Downtown Woodstock
Downtown Woodstock is as cute as a town can get. It’s perfect for a slow afternoon stroll along Main Street. If you’re visiting in season, don’t miss the Mower’s Flea Market on weekends, where you can browse vintage finds and local crafts.
Overnight Stay Ideas
KEEP THE ADVENTURE GOING WITH A STAY THE NIGHT AT AutoCamp CATSKILLS
If you don’t want your day to end enjoying the outdoors, AutoCamp Catskills makes for a fun and stylish overnight stay that you and your dog will love. Their modern Airstreams and cabins look effortlessly cool, each with cozy interiors, fire pits, and just the right mix of comfort and adventure. It’s a great way to extend your Kingston and Woodstock getaway and wake up surrounded by nature.
BOOK A QUIET OVERNIGHT GETAWAY AT Woodstock Way Hotel
In the heart of town, Woodstock Way Hotel blends nature and design in a beautifully calm way. And yes, dogs are welcome in designated rooms, so they don’t have to miss out on the getaway.
THE ART OF TRAVELING LIGHT FOR YOUR OVERNIGHT
For quick Hudson Valley getaways, packing light makes all the difference. We love traveling with our LEVEL8 Gibraltar Aluminum Carry-Ons. They’re durable for all our adventures and perfectly sized for a one or two-night trip. We brought our his and hers with us, and they looked just as good in the trunk as they did in our hotel room. If you’re curious about how it holds up on the road, you can read my full, honest review here.
Final Thoughts
This little corner of the Hudson Valley, Kingston and Woodstock, always feels like a breath of fresh air. Whether you make it a full day or stretch it into an overnight stay, it’s the kind of trip that reminds you to slow down, explore at your own pace, and enjoy the simple moments with your dog by your side.
For more day trip ideas from New York, check out my other blog posts:
3 Unique Day Trips from NYC That Will Inspire You
Escape to Upstate New York: Memorable Day and Weekend Getaways
One Perfect Day in Hudson: A Dog-Friendly Haven in Upstate New York
3 Amazing Winter Trips to Upstate New York from New York City
Greenport, NY Getaway: How to Enjoy a Day on Long Island’s North Fork
✧ For the intentionally curious traveler — pass it on.