The Ultimate Weekend Guide to Kingston, New York

I almost didn’t write this blog post about Kingston, New York.

Why?

Because selfishly, I want to keep this charming, historic town to myself! Kingston, New York, has captured my heart. So much so that I’ve already traveled back numerous times since my first visit there with a few girlfriends.

Now, I want to share all of my discoveries from Kingston, New York, with you. Whether you’re looking for an easy weekend getaway from NYC or you’re on a longer trip exploring the Catskills and the Hudson Valley, make sure this town is on your list!

Where is Kingston, NY and How Do You Get There?

Kingston is located in the Hudson Valley, about 90 miles north of New York City. It sits in the heart of Ulster County, bordered by the Catskill Mountains to the west and the Hudson River to the East.

The most direct way to Kingston is by car. Depending on traffic, it’s less than a 2 ½ hour drive from New York City.

There are also multiple train/bus options. You can take an Amtrak train from Penn Station in New York City to either Poughkeepsie or Rhinecliff and then a bus or car service to Kingston.

So, what is there to love about Kingston, New York?

A lot, as it turns out!

The city is full of history and interesting architecture. It has a buzz-worthy food scene and boutiques selling everything from bespoke home goods to country-chic clothing and hot sauce (Yes, you read that correctly!).

Kingston also has a surprising history. The city was first settled by the Dutch in 1658. And fun fact – did you know that in 1777, Kingston was designated as New York’s first capital? That title was short-lived, as the British burned down much of the town the same year after the Battle of Saratoga. In the 19^th century, the city became a bustling transport hub in the region before falling on harder times.

Today, a revitalization is taking place. Kingston is now home to many artists, creatives, and entrepreneurs who have transformed all three parts of the city into unique and thriving neighborhoods. This once under-the-radar Hudson Valley town is a flourishing region that people are flocking to, including me!

Last but not least, Kingston is surrounded by nature. From the gorgeous Hudson Valley countryside to the Catskill and Shawangunk Mountain Ranges rising in the West, there are plenty of activities for outdoor enthusiasts, including hiking trails, local ski mountains, and the Empire State Trail runs right through town.

Pro Travel Tip: If you’re planning an upstate trip, check out my blog posts about Woodstock and Livingston Manor.

Getting Around Kingston

Part of what makes Kingston, New York, unique is its three distinct neighborhoods. There is Uptown Kingston, also known as the Stockade District, Midtown Kingston, once the heart of industry for the city, and Downtown Kingston, also known as the Rondout or waterfront. You can’t easily walk between the three districts. However, it’s only a 10-minute car ride from Uptown to Downtown Kingston. Each of these neighborhoods in Kingston has a distinct vibe and feel to it.

Uptown Kingston – This part of Kingston includes the Stockade National Historic District. From Dutch-inspired buildings and 17th-century stone houses to Wall Street’s colorful row of storefronts, there’s something to see everywhere you turn. This part of Kingston is full of boutique shops, restaurants (including my favorite, at the Kinsley Hotel), yoga studios, tattoo parlors, art galleries, and more.

Midtown Kingston – Once the industrial section of Kingston. Midtown is now an up-and-coming, eclectic mix of restaurants, mom-and-pop shops, and residential neighborhoods. It’s also where you’ll find many of Kingston’s murals or street art. (More on this below.)

Downtown Kingston – Also known as the Rondout. This part of Kingston sits at the edge of the Rondout Creek, a tributary of the Hudson River. This part of town boasts waterfront views and is filled with hip eateries, wine bars, and locally owned businesses.

Where to Stay in Kingston

Hotel Kinsley – This bespoke hotel is spread across four 19th-century buildings in the Stockade District of Uptown Kingston. It includes a chic restaurant and cocktail bar and is the perfect escape for design lovers.

Hutton Brickyards – A collection of luxury cabins with views of the Hudson, this hotel in Downtown Kingston provides a relaxing and imaginative retreat for travelers.

Airbnb – There are also plenty of great Airbnb options in the area, which provide more flexibility if you’re traveling with a larger group. Every time I’ve visited, I’ve stayed in an Airbnb. But the next time we visit, Hotel Kinsley is at the top of my list!

Where to Eat & Drink in Kingston

Kingston Bread and Bar – Located on Front Street in Uptown Kingston, this bread bar offers artisanal bread and pastries, plus sandwiches and coffees. It’s a great spot for a quick, casual breakfast or brunch.

Village Coffee and Goods – Located in Midtown Kingston, this hip coffee shop turns out amazing breakfast sandwiches and platters, along with baked goods. They also sell a curated selection of local pottery, serving ware, printed cards, and more. We also loved this place because they allow dogs in their small dining room adjacent to the coffee shop.

Diego’s Taqueria – Who knew you could find really good Mexican food in Kingston, New York? If you’re in the mood for tacos and margaritas, hit up Diego’s for a Mexican feast in a laid-back setting.

Sweet Maresa’s – In Uptown Kingston, this bakery is a welcoming spot with an array of baked goods, including gluten-free options like their pastel-colored macarons.

Lola Pizza -If you’re looking for a hip and casual spot for lunch or dinner, head to Lola Pizza in Uptown Kingston. The restaurant offers a long list of individually styled pizzas, pasta, (gluten-free pasta too!), and salads.

Brunette Wine Bar – A chic wine bar in downtown Kingston that specializes in natural wines along with interesting food pairings. We loved how knowledgeable the staff was about natural wine.

Hotel Kinsley – One of our favorite eateries in Kingston, we love everything about this restaurant from the aesthetics, the cocktails, the food, and the attentive waitstaff. If you make it to Kingston, eating here is a must.

The Winter Pavilion at Hutton Brickyards – The seasonal restaurant at the Hutton Brickyards just outside of Downtown Kingston makes good use of its expansive, industrial-style event space. We loved our meal here as much as the people watching. An added bonus is the s’mores desert, which you can enjoy at your table or outside at the fire pit.

Stockade Tavern – Every town deserves a bespoke cocktail bar, and in Uptown Kingston, Stockade Tavern is the place to go for a wide range of inventive and tasty cocktails.

Where to Shop in Kingston

Hamilton and Adams – A hip boutique that I could just as easily see in Brooklyn, this shop has a curated selection of women’s and men’s clothing, plus a unique collection of sweatshirts and t-shirts with logos like ‘Upstate & Chill’.

Rough Draft Bar and Books – A book store that also has a coffee and wine bar? Sign me up! We loved visiting this book store. We would have spent an hour or two in a cozy corner, sipping on a matcha latte, if it wasn’t for the large crowd of people who had the same idea!

Spruce  – a very stylish and well-curated furniture and home goods shop in Downtown Kingston. While I wanted to buy one of everything, I settled for a couple of scented candles. They also have a sister shop, Exit Nineteen, located in Uptown Kingston.

Clove & Creek – a stylish shop selling items for the home, apothecary, local goods, and coffee. They have a second location in Hudson, New York.

Village Grocery & Refillery – Run by the same owners of Village Coffee and Goods, this specialty food market in midtown Kingston is fully stocked with artisanal cheeses, pastries, cured meats, and fresh produce, and more. They also make delicious breakfast sandwiches and lattes.

Things to Do in Kingston

A Walking Tour of the Historic District – On the first Saturday of the month, July 2^nd through October 30^th, the Friends of Historic Kingston conducts a free walking tour of Kingston’s historic district.

The Empire State Trail – Take a walk or a bike ride on the Empire State Trail, a protected pedestrian and bike lane that spans 750 miles across the state of New York and runs right through Kingston.

Kington’s Murals – Take a self-guided walking tour of Kingston’s murals. The artwork was commissioned by O+, a nonprofit founded in Kingston in 2010. The organization empowers communities to take control of their collective wellbeing through the exchange of art, music, and wellness.

The Kingston Farmers Market – This year-round farmers market in Uptown Kingston is open every Saturday. From May to November it’s outside. During the winter months, the local vendors set up shop in various indoor locations. Always check the website for the most up-to-date information.

The Ulster Performing Arts Center – Catch a show at the Ulster Performing Arts Center in midtown Kingston, where you can see everything from live music, dance performances, or a comedy event.

Explore the Hudson River – If you visit Kingston, NY during the warmer months, rent a kayak or canoe from A Day Away Kayak Rentals or a sailboat from Tivoli Sailing Company.

Are You Ready to Visit Kingston, New York?

So, what do you think?

Are you ready to pack your bags for a fun weekend getaway to Kingston, New York? I hope this post has inspired you to visit this charming city.

I love Kingston so much and can’t wait to visit again soon. Who knows, maybe I’ll even see you in town!