A Weekend in Kingston, NY (With Kids)

Spring break this year had to be local again. But rather than being disappointed, I was looking forward to exploring more of upstate New York. International jetsetting is glamorous, but nothing beats a trip that’s only 1.5 hours away by car. This time around we made Kingston, NY our base. Kingston, compared to Fishkill, which was the town we stayed in on our winter break, felt more like a proper town. We stayed in an Airbnb rental right in the heart of downtown, and I couldn’t have been happier. I loved the fact that we were within walking distance to a lot of great restaurants, bakeries and coffeeshops, and there were a lot in the immediate area! Kingston is also a good base for exploring other nearby towns like Rhinebeck, Saugerties and Woodstock, which are ~20 minute drives away. The kids, as always, loved being in a bigger house than their city apartment, and it was fun taking them on scenic hikes and train rides in the Hudson Valley. A weekend trip to Kingston with the kids is always a good idea, especially when the weather gets nicer. Here’s a sample itinerary of things to do if you choose to take the kids to Kingston NY on your next quick trip out of the city.

Day 1
Settle in with a book, and maybe a beer, at Rough Draft Bar & Books
Rough Draft Bar & Books // 82 John St, Kingston, NY 12401 // (845) 802-0027


After driving in from the city, you can settle into your day with a good book in hand at Rough Draft Bar & Books, a local bookstore with a carefully curated selection of books. Their children’s selection is actually pretty great, so your toddler will also have something fun to read. What’s great about this store is that, not only do they serve coffee, but they also have beer on tap. It feels like a real hangout, what local bookstores used to be during the heyday of Borders Bookstore and Barnes and Nobles. Sadly, these bookstores are now a dying breed, which makes it even more essential to support a place like Rough Draft. Currently indoor seating is very limited, so it’s best to buy your book (and beer) and read it outdoors at one of their tables.

Afternoon snack at Sweet Maresa’s
Sweet Maresa’s // 291 Wall St, Kingston NY 12401 // (845) 663-2000

Sweet Maresa’s is simply irresistible with its cute blue awning and the lovely smell of cookies and pastries wafting through its door. Its specialty is macarons, but I was extremely impressed with their cookies in general. Their flavor combinations are unique and enticing, and the desserts are quite pretty. Sometimes things that look pretty taste pretty meh, which I hate, but the cookies at Sweet Maresa’s are not like that. I would recommend the pistachio and oreo cookies for sure. I also learned that Sweet Maresa’s operates a co-owned bakery called Confectionary! in New York City in the East Village, which was exciting news. It’s nice to have a little bit of Kingston in the city.

Spend the day with animals at Forsyth Nature Center
Forsyth Nature Center // 125 Lucas Ave Ext, Kingston, NY 12401 // (845) 339-3053

Thank god for the Forsyth Nature Center, which was about a 10 minute walk from our Airbnb rental. This center houses two-dozen animal exhibits that are available for viewing to the public FOR FREE. And for that price, it was the most high quality animal center that I have ever been to. These are not just pigs and chickens running around a barn. There are exotic animals like alpacas and beautiful peacocks on site. I was very impressed, as was my son by the majestic peacocks. Even better is that there is a wonderful playground on site as well. Your kids would probably be so happy coming here everyday.

Eat delicious pizza and pasta at LOLA Pizza
LOLA Pizza // 243 Fair St, Kingston, NY 12401 // (845) 768-3624

The pizza at LOLA Pizza is incredible. The crust in particular is phenomenal–doughy, chewy, perfectly blistered from its time in a wood fired oven–that you actually eat it as opposed to tossing it off to the side as adults tend to do. I think LOLA knows its crust game is strong, so they feature it prominently in the stracciatella appetizer, in which a huge pouf of crust is served alongside some creamy cheese. The cheese is so good, my son thought it was ice cream. The wood-fired oven was imported from Naples, so you know this place is legit. LOLA could definitely hold its own against a Roberta’s or Motorino in Manhattan. In fact, one of its pies, the Tiger Paw, reminds me a lot of the famous Bee Sting pizza at Roberta’s. A pepperoni pie with a little honey for sweetness and just a dose of jolting spice.

Don’t write off the pastas. They are rustic and homey and make you feel happy to be there. Nuggets of cavatelli with short rib meat nestled throughout, for when we are still transitioning out of the winter months. Long strands of mafalde paired with generous crab meat and asparagus, heralding spring. It all sounds and tastes very wonderful, so you need to make room for these dishes, and you will.

Day 2
Enjoy delicious pastries and coffee at Kingston Bread + Bar
Kingston Bread + Bar // 43 N Front St, Kingston NY 12401 // (845) 802-0021

Kingston Bread + Bar without a doubt makes the best bread and pastries in the city. I was absolutely obsessed after I tried their amazing chocolate raspberry almond croissant and miso tahini cookie. I also loved this newfangled pastry creation they came up with called the Bostock, which is basically almond croissant filling on top of Japanese milk bread. It sounds like the best of both worlds and it is. They are absolutely on par with the artisanal bakeries that operate in New York City. Think places like Partyhouse Bakeshop or Mel Bakery. Their hours are a bit limited. They are currently only open Wed – Sun, and the selection is much wider on the weekends, so plan accordingly!

A leisurely train ride on the kitschy Catskill Mountain Railroad
Catskill Mountain Railroad // 55 Plaza Road, Kingston Plaza, Kingston, NY 12401 // (845) 332-4854

Children and train rides go hand-in-hand, and luckily, the Catskill Mountain Railroad is just in town. If you’re expecting a scenic road through gorgeous valleys and mountains, this is not quite it. You will pass by construction sites and a Hannaford. But if you want something to occupy the kids for an hour, then this is just the thing. What’s great about the Catskill Mountain Railroad is that their rides are themed, so depending on when you go, you could be going to the North Pole or meeting the Easter Bunny. Meeting the Easter Bunny and getting candy from him/her was pretty great for the kids.

Lunch in Rhinebeck
The Amsterdam // 6380 Mill St, Rhinebeck, NY 12572 // (845) 516-5033

As I mentioned before, Kingston is a good base for exploring other towns like Woodstock, Saugerties and Rhinebeck, all of which are worth a visit. Rhinebeck is probably the most grown up out of the bunch. When you walk around Rhinebeck’s downtown, you definitely notice how things are a little nicer. If you want to eat in style, head over to The Amsterdam, an excellent New American restaurant that serves elevated farm-to-table fare in the Hudson Valley. It’s like being invited over to a nice lunch at your rich friend’s parents’ stylish country house. The house made ricotta with seasonal spring peas and duck prosciutto was excellent, as was the pate. The lunch special is a great deal that allows you to try half a sandwich and a soup or salad. I would highly recommend the grilled chicken panini, and if a pea or asparagus soup is offered, get that as well.

Dinner at Restaurant Kinsley
Restaurant Kinsley // 301 Wall St, Kingston, NY 12401 // (845) 768-3620

Maybe it’s a sign of the times when a slick boutique hotel moves into your town, but thank goodness for the Hotel Kinsley in Kingston. The style is definitely more modern and downtown than rustic and upstate, but it’s nice to have a place like this to go to that’s nearby. While Restaurant Kinsley feels very “New York City”, the food is all locally sourced from the Hudson Valley and features New American classics that change seasonally. Expect to see lots of produce dishes like beets and squash or whatever is in season at the time, and some standard crowd favorites like roast chicken or steak. The roast chicken is pretty phenomenal and very plentiful, so that made me very happy. There’s something for everyone to choose from, and the whole dinner party will leave very satisfied. The cocktails are very good, but also extremely strong, so exercise caution!

Day 3
Easy hike at Falling Waters Preserve
Falling Waters Preserve // Dominican Ln, Saugerties, NY 12477 // (845) 473-4440

No trip to upstate New York is complete without a trip to a farmer’s market or a hike of some kind. There are plenty of challenging trails that take hours to complete, but with young kids, that is not an option. Falling Waters Preserve, on the other hand, has a super easy trail that navigates you directly to picturesque waterfalls and an open meadow with views of the Catskills. It’s also a quick drive from Kingston, which makes for a great day trip. Take a picture in front of a waterfall and instantly look like you stepped on to the pages of Welcome to the Hudson Valley. It’ll probably take you 15-20 minutes to complete, and after that, it’s time for brunch!

Brunch at Miss Lucy’s Kitchen
Miss Lucy’s Kitchen // 90 Partition St, Saugerties, NY 12477 // (845) 246-9240

By 11 am, Miss Lucy’s Kitchen was starting to fill up. I can only imagine how packed this restaurant would be during the peak summer months. It has that look and feel of a perfect brunch spot–homey and comfortable with lots of wooden tables and chairs that felt lived in, a sign that this place has been around for awhile and knows what they’re doing. Although on the day we went, they were out of a lot of things. Like fries and fried chicken. The fries outage was particularly heartbreaking. The dandelion greens caesar salad was decent though, as was the fried chicken cutlet sandwich. Next time I would skip the house made spreads and the pea soup.

Ice cream, pizza and a walk through downtown Woodstock
Sweet Dreams Organic Ice Cream // 74 Tinker St, Woodstock, NY 12498 // (845) 684-5910
Catskill Mountain Pizza Co // 51 Mill Hill Rd, Woodstock, NY 12498 // (845) 679-7969

Woodstock brings to mind the iconic music festival that epitomized the free-wheeling 60s. Some of that hippie spirit can still be felt in the downtown stores that sell tie-dye shirts and in the quirky veganish eateries, although Woodstock has also gotten much fancier since then. When the kids start getting restless, you can take them to Sweet Dreams Organic Ice Cream, which was open in the spring. The ice cream here is surprisingly expensive, and I wouldn’t say it tasted better than comparably priced scoops in the city. But it’s open and there are lots of flavors to choose from.

If you choose to stay here until dinner, a pizza meal at the modest Catskill Mountain Pizza Co could be a good option. The pizzas are huge and reasonably priced, and they allow you to mix and match toppings on a single pie, which is a big win for big families. I would say the pizzas are solid–not on the level of LOLA’s–but the kids will be very satisfied. Note that they are cash only.