A Wintry Weekend in Kingston, NY

Hello dear readers! I recently shared some wonderful places to visit for a long holiday weekend getaway from NYC. Over Presidents’ Day weekend, we escaped the city briefly ourselves, though we kept our travels close to home and on the short side this year so we could still enjoy our Monday off at home. We decided to venture to New York state’s first capital, Kingston, NY, so that we could spend a bit of time exploring the beautiful Hudon Valley. And what a lovely weekend we had!

How to Get to Kingston, NY

Uptown Kingston

Kingston is just about 100 miles from New York City, making it a great place to visit for a long weekend. Even in the wintertime, the Hudson Valley is stunning, but you can’t really appreciate its natural beauty quite as well from the highway. Certainly, if you’re in a hurry, you can get to Kingston on I-87 in just about two hours. However, I would actually suggest that you take a longer but far more scenic route to get there. 

You can get to Kingston from either side of the Hudson River, and both sides offer beautiful views of the river, the Palisades, and the Catskills, not to mention all the adorable little towns that dot the road on your way up north. If you decide to drive up the east side of the Hudson, take Route 9 and then 9D to keep close to the river and drive through all the river towns like Sleepy Hollow, Cold Spring, and Beacon. Once you get to Poughkeepsie, cross the bridge and finish your journey on the west side of the Hudson River.

Or, you can make your whole journey up the west side of the Hudson River along 9W. Again, this will keep you closer to the river and allow you to drive up through the majestic Palisades, passing by places such as Bear Mountain, West Point, Storm King, and Newburgh.

The west side starts out at a higher elevation, offering incredible views of the river below, but the east offers a better view of the Palisades and the mountains. Either way, if you want a scenic drive to be part of the fun during your weekend away, skip the highway and use one of these options instead!

What to Do In and Near Kingston, NY

We had been to Kingston briefly once before and knew we wanted to go back for a longer stay at some point. Though a lot of the local attractions are closed during the winter, there is still plenty to do in the off-season in Kingston, as well as in nearby towns.

  • Explore The Rondout and the Waterfront: The lower end of Kingston is known as The Rondout. Once a separate town, Rondout and Kingston were incorporated together as just Kingston in the 1870s. Today, there are plenty of restaurants, bars, and shops here along the Rondout Creek. It’s definitely a little sleepier in the wintertime, but it’s still fun to peek into the shops or take a walk along the creek on a crisp winter day.
  • Hudson River Maritime Museum: In Rondout, you can also visit the fantastic Hudson River Maritime Museum, which is situated right alongside the creek.  In the wintertime, you can visit their museum exhibits or participate in their lecture or film series. The museum also offers boat trips and walking tours from May to October when you can take a boat out to the nearby Rondout Lighthouse.
One of the ships outside the Maritime Museum
  • Stroll Around the Stockade District: When you’re done exploring downtown in The Rondout, head back uptown to the Stockade District. Here you’ll find the famous Four Corners, which is an intersection where on each corner sits a house that was built in the 17th century (it’s the only intersection of its kind in the U.S.) There are also plenty of places to stop for a bite, a couple record stores, art galleries and more to keep you busy for a while. You can also do this self-guided walking tour to make sure you see all the highlights.
One of the 17th-century houses at the Four Corners
  • Admire Kingston’s Beautiful Murals: Kingston is home to the O+ Festival, which is sponsored by an organization that helps to connect artists with health and wellness professionals. Each year, many of Kingston’s buildings become a fresh canvas for one of these artists to leave his or her mark. You won’t be able to walk around Kingston without noticing all the murals, but you can also use this handy map if you want to be sure you find them all!




  • Take a Drive to a Nearby Town: Kingston is also a great home base for visiting other Hudson Valley towns. The last time we visited Kingston we had actually been staying in New Paltz, which is only about 20 minutes away. There you can take a winter hike if weather permits or enjoy a cozy lunch at the Mohonk Mountain House or one of the many fantastic restaurants in town. This year, we ventured north instead to check out Woodstock and Saugerties, neither of which I’d had an opportunity to visit before. Both towns have excellent art galleries and boutiques, and there are plenty of breweries, wineries, and distilleries scattered throughout the area, too, if you need a little something to warm yourself up!
Downtown Saugerties
  • Visit Kaaterskill Falls: A lot of people think visiting waterfalls is a warm-weather activity, but my friends, I beg to differ! In the wintertime, waterfalls become magical ice sculptures, and Kaaterskill Falls is no exception. The drive up to the falls is spectacular, though you’re going to want to save this visit for a good weather day, as driving could be treacherous in the snow. Head up to the parking lot for the upper falls, and it’s not even a half-mile walk down to the viewing platform. If you’re feeling really adventurous (and have the appropriate gear), hike on down to the bottom! 
Kaaterskill Falls
  • Take the Five Locks Walk: Before we headed back to the city, we stopped in High Falls, NY to visit five abandoned locks from the old D&H Canal. If you’ve been following along for a while, you’ll recall that we spent a fantastic week houseboating the Erie Canal a couple summers ago, so we were pretty excited to go check out the Five Locks Walk. Here though, there’s no canal left anymore, but you can walk along the one-mile trail to see what still remains of the old locks. It’s hard to imagine a canal cutting through there nowadays, but you can definitely get a sense of how boats would have once made their way up and down the hills between the Delaware and Hudson Rivers.
The old D&H Canal seen from the Five Locks Walk in High Falls, NY




Where to Eat and Drink

With all the sightseeing you’ll be doing in Kingston, you’re going to need to take some breaks to refuel! Don’t worry, though, there are plenty of yummy places to eat and drink.

  • Blondie’s Trolley Diner: If you’re looking for a serious locals’ spot, Blondie’s Trolley Diner is the place for you. It’s housed in, you guessed it, a trolley! This is definitely a greasy spoon, but I watched them make the gravy for my biscuits and gravy right before my eyes. No ladling old, scummy gravy out of a pot in the back at this place. And it was delicious!
  • PAKT: We were supposed to have free breakfast at our hotel, but it was so overrun with people that we decided to head into town instead. We discovered a cute spot called PAKT and arrived right as they were opening. I had one of the daily specials, the “red” velvet cake french toast. It was insanely delicious but it resembled carrot cake more than red velvet (and definitely wasn’t red!) They also had some extra tasty coffee cocktails if you need a little more than caffeine to perk yourself up in the morning.
Red Velvet Cake French Toast from PAKT
  • The Anchor: If you’re in the mood for a juicy burger, head over to The Anchor, whose menu features more than a dozen different types of burgers. The place was PACKED and we had no reservation, but we were able to snatch up the last table remaining in the bar area. These are first-come, first-served, so if the place looks crowded and you see one of these open, grab it! And then grab yourself the french onion burger because it was soooo good.
The french onion burger from The Anchor. Look at all that glorious cheese! And a little cup of french onion soup on the side for dipping.
  • Breweries: If you’re ready to wash down your burger, there are three breweries in Kingston, all of which have a completely different vibe. Keegan Ales seems to be the oldest brewery in Kingston, and they also have the most expansive food menu and live music. We enjoyed the beers the most at Great Life Brewing and would have stayed for a pint after finishing our flight, but it was so crowded and there wasn’t really anywhere to sit or any snacks. Eventually, we made our way over to Kingston Standard Brewing, which had lots of room to sit but didn’t offer flights. They did let us sample a couple things and we settled in for a bit with our pints. They have pizza, oysters, and some other snacks, too, if you need a little something to munch on while you enjoy your beer.

Overall, we had a short but wonderful time in Kingston and the surrounding area. It was sunny and beautiful on our drive up and remained warm for our second day and clear for the drive home. The temperatures were in the upper 30s and low 40s, but we wore our boots and warm winter coats and found it perfectly enjoyable to be outside.

Most of the area attractions that close for the winter will reopen in May, so if you want to enjoy beautiful Kingston without the rest of the summer travelers, head on up there sometime soon!

One Comment Add yours

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s