I am single, nearing 30, and in love with Webster, my overweight basset hound. Until recently, I had become resigned to the fact that our slobbery relationship would always be in direct opposition to the next biggest obsession in my life: travel. Fortunately, there are the Catskills, an easily accessible and enjoyable trip for outdoorsy travelers — especially those with a dog in tow.
The small towns that make up the Catskills are a place where farm-to-table isn’t just a buzzword, it’s a way of life. A land where you remember that driving can actually be an enjoyable experience. The area bursts with history, homesteads, and a whole lot of hippies. Here’s how to plan a drool-proof trip to upstate New York.
How to get there
Driving puts all of the picturesque towns of the Catskills and Hudson Valley within reach and ultimately gives you the most flexibility. If you don’t have your own vehicle, schedule a rental from your starting location or take the train to a town along the Hudson River and grab a rental from there.
If you’ve decided against renting a car, pick one town as your home base and plan to do most of your exploring around that area. Woodstock and Hudson are both teeming with shops, restaurants, and outdoor activities.
Where to stay
- There’s nothing like a great Airbnb to make you feel a part of the community. For those with pets, the website’s filters make searching for pet-friendly spots ridiculously easy. Just be sure to thoroughly read the listing’s description as some have restrictions on size or type of animal.
- If you’re traveling with a group or with a dog, try the Clum House ($275/night, sleeps 5) in Catskill (the actual town), conveniently located between Woodstock, Saugerties, and Hudson. At night, I rested in front of a roaring fire — all I needed to do was strike a match. Side note: the full property used to be a girls’ summer camp and can also be rented out for the upstate wedding of your dreams!
- Arbor Bed & Breakfast (from $135/night) to sleep in a renovated 1890 farmhouse which allows small dogs and kids.
- The Catskills offers numerous outdoor camping sites, including the lakeside Bear Spring Mountain ($18/night) campground.
- New Paltz’s Mohonk Mountain Lodge ($440/night) is epic in proportions and rumored to be the influence for Stephen King’s The Shining.
Where to eat
For breakfast and lunch, hunt out spots with outdoor seating, preferably with direct exposure to the warm winter sunshine. While Hudson may technically be in Hudson Valley, I am counting it within this itinerary if only so I can sing from the rooftops about the best dining experience I have had in years.
- One step inside Lil Deb’s Oasis (mains $10-24) and you understand the inspiration for the name. This small restaurant, a beacon of neon-streaked personality, stands in stark contrast from most other upstate hotspots which tend to lean towards a streamlined minimalist or rustic hipster aesthetic. The self-proclaimed tropical comfort food is fresh and inventive. The staff are so welcoming and genuinely themselves that you may have the startling realization that you’ve never actually felt at ease in a restaurant before.
- Cold Springs: In winter, not much opens before 11am in Cold Springs. But a great breakfast can be found at Cupoccino Cafe(mains under $10).
- Woodstock: For those who prefer a flaky buttermilk biscuit sandwiching egg, ham and melted cheddar, head to Shindig (breakfast $4-11). ) Sunfrost Farms. Is an option for those wishing to grab a quick meal or peruse organic foods in a market setting.
- Kingston: Vegetarian coffeeshop meets antique store at [outdated] (mains $5-12), where everything (including the chairs you sit on) is for sale. While you’re in Kingston, don’t forget to stop by the Kingston Candy Bar. On top of the store’s very impressive roster of sweetened nostalgia, the owner, Diane, makes a limited batch of uniquely designed (and pop culturally on point) donuts every day and bakes dog treats from scratch. )
What to do
- Hunt for vintage. Strike a bargain or find a hidden gem at one of the many antique stores upstate. Each town has its own offerings of vintage clothing, furniture and knick-knack stores.
- Shop small. Peruse the local stores lining the main streets in these small towns. My wallet goes into hiding whenever I pass a bookstore, so it’s not surprising I came home with quite a few new additions to my library. As with many small store owners, the bookstore employees are a goldmine for local information and recommendations. At The Golden Notebook in Woodstock, we were enthusiastically received by Delta the bookstore dog — and I couldn’t help but pick up a $1 Judy Blume classic at Half Moon Booksin Kingston.
- Enjoy nature. Go for a hike! Ride a bike! Hug a tree! The Catskills have trails for every skill level and thrill-seeker. At the Comeau Trail in Woodstock, enjoy a peaceful riverside stroll through the woods. The park is free to the public and open to dogs off-leash and feels secluded despite its convenient location minutes from downtown Woodstock. The path is a loop that can be done in under 20 minutes (or an hour if you’re walking a hound).
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