Mini Upstate Getaway
Woodstock, Saugerties & Kingston - A winter itinerary
I used to think a cold-weather weekend getaway must require a plane ride to be considered a “real” vacation. But my newest little secret is Ulster County - so many visit worthy towns to check out, AND only a little over an hour from Westchester. One Tuesday in early January, before my two daughters headed back to college, we took a 30-hour escape to Woodstock, Saugerties, and Kingston. We managed to hike, eat, shop, walk, learn some history, walk, and snack as we explored. Below is our itinerary:
DAY 1
9:00 - Hike Overlook Mountain
We left the house at 7 am (breakfast in tow!) and made it to Overlook Mountain in about an hour and 15 minutes. This trail received excellent reviews, and you can do it in just under 3 hours. While not too challenging, it is quite steep in places. As we got closer to the top, we came across the ruins of Hotel Overlook, built in the 1800s but eventually abandoned due to its difficult location. A bit further up, we arrived at the ledge, also known as “the cliffs,” where the view was absolutely breathtaking. As we got closer, we gasped at the sight of what lay below – the Hudson River, Ashokan Reservoir, and the Central Catskills. Apparently, on a clear day, you can even see as far as Massachusetts! And if that weren’t enough, slightly back from the cliffs, we found the Overlook Fire Tower, which we climbed for even more stunning views of the Catskills.
11:30 - The Karma Triyana Dharmachakr,
If you have time, check out this Buddhist temple directly across from the trailhead parking lot. You will feel like suddenly, you’re transported to a Tibetan Mountainside. The girls were getting hangry, so we skipped it, but it’s a welcoming retreat with a pretty special gift shop with a big collection of Buddhist books and lots of Tibetan art.
1:00 - Lunch at Oriole 9 in Woodstock
Because we were starving, it was one of those family situations where none of us could agree. Phil, my husband, wanted Yum Yum Noodle Bar. Clementine wanted Bread Alone Bakery. We were seconds away from splitting up when we came across Oriole 9, which had something for everyone. I recommend the tempeh caesar salad👌, but the grilled reuben was delicious if you prefer something heartier. And sandwiches come with gluten-free bread options.
2:00 - Browse through the cute shops on Tinker Street
Tinker Street is the main drag in Woodstock, lined with lots of crafty jewelry stores and candle shops, most of which were closed since we were there midweek. My daughter, Scarlett, who seems to find something she wants to buy anywhere we go, managed to spot a hippy, flowing skirt, and I picked up a few Grateful Dead stickers for my sister.
4:00 - Walk around Saugerties
We still had lots of daylight left, so we moved on to the next spot. Saugerties is a sleepy little town with two main streets, each about three blocks long. In true upstate form, everything has been around forever, and not a chain store in sight. Between Montano’s Shoes and Inquiring Minds Bookstore, I felt like I was stepping back in time (in a good way!). Montano’s reminded me of Harry’s on the Upper West Side – great service, plenty of options in stock, and family-run for more than 100 years! Over at the bookstore, there was a huge selection of New York-related books. The uneven wooden floors reminded me of The Strand. The girls had to drag me off the comfy leather couch, where I started reading “The History of Saugerties.”
5:00 - Head to the Saugerties Light House for sunset!
Just as the light started to fade, we visited the Saugerties Lighthouse. A narrow half-mile trail surrounded by overgrown bushes, tidal pools, and wildflowers led us to the lighthouse itself. Built in 1869 to warn ships on the Hudson of shallow waters near the mouth of the Esopus Creek and renovated in the 1990s, the building is now a museum with tours in the summertime, and you can even book a night in their bed and breakfast. The sunset views were stunning!
6:00 - Check into Hotel Kinsley in Kingston
Hotel Kinsley is a collection of four renovated buildings in the Stockade District. The main building is in a former Bank of New York – you check in at the front desk, which is located inside the former bank’s vault! Our mid-century furnished rooms were in a building a couple of blocks away on Fair Street – you would never know it had once been a former gas fitting factory.
7:00 - Cocktails and dinner at the Hotel Kinsley Restaurant
Chef Zak Pelaccio developed the locally sourced comfort food menu for the hotel’s restaurant in the bank’s former lobby. There are five entrees to choose from, all equally good! I went classic with a cheeseburger and sautéed kale but kept stealing bites from my daughter’s three-mushroom pasta. The big, cozy room with orange velvet banquettes and a fireplace in the center was a great escape after a cold winter day.
DAY 2
8:00 - Head out for a walk in Kingston’s Historic Stockade District
Stop and read the landmark markers and plaques to learn about the stone buildings and their significance. Don’t miss The Four Corners Intersection, the only place in the whole country where 18th-century houses stand on all four corners (who knew?). The Senate House on Fair Street, built with typical Dutch stone architecture in 1676, is the oldest public building in NY and is one and a half stories tall.
10:00 - Grab a coffee at one of two spots:
Rough Draft Bar & Books - possibly my husband’s favorite place in the world - where books surround you in an airy space. Or Kingston Bread + Bar for artisanal breads and flaky croissants. FYI: The Rough Draft old stone building was the first two-year college in New York State.
11:00 - Shopping in Kingston
Most stores open around 11:00 am. Some of my faves are Rivermint Finery for high-end women’s clothing, Hamilton & Adams for an “Upstate & Chill'' sweatshirt, and my favorite perfectly curated kitchen store, Blue Cashew, where even a new garlic press feels like something I must buy. Kingston Consignments, has two overflowing floors, jam-packed with vintage clothing, kitchenware, decorations, and furniture. The day I went, I found four old-school Nick and Nora glasses.
1:00 - Lunch at Village Coffee in midtown
This spot has excellent quinoa bowls that change daily – mine had bok choy, kimchi, and a fried egg. They also sell provisions like locally sourced bread and cheese; And beautiful ceramics by L’iimpatience, Tellefsen Atelier, and other Hudson Valley potters.
2:30 - Walk along the Roundout Waterfront
Check out the Hudson River Maritime Museum. Yes, it’s small but packed with information about the importance of the port and the local building materials industry in Kingston.
4:00 - One more snack before hitting the road
Rosie General is kind of a deli, sort of a bakery, and a little bit of a grocery store. We each picked up a car snack, choosing from baked goods and thickly sliced sourdough sandwiches. I must say, the slice of olive oil lemon cake was exceptional.
And if you aren't driving, head over to Brunette Wine Bar, which has natural wines from all over the world. Get the Trout Roe Nachos! Who doesn’t like caviar on a potato chip?
For more on Kingston, see my round-up here.
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