Keap’s Guide to Kingston 2026

A shortlist of our favorite places in our historic Hudson Valley hometown

colorful buildings in Kingston's historic Uptown District
Kingston's Historic Uptown District. (Photo: Keap)

Nestled between the Catskill Mountains, the Rondout Creek and the Hudson River, you’ll find our historic city of Kingston. Once the capital of New York State, and now our home and headquarters!

Below is our shortlist of must-see and favorite Keap-approved spots for anyone visiting our hometown. We hope you enjoy your visit and get to see why we love it here so much. If you have any feedback or recommendations you want to share with us, please let us know!

SEE

Brick building with the name of gallery written in front " Headstone" in silver
Headstone Art Gallery. (Photo: Keap)

Kingston Farmer's Market

For a vibrant scene every Saturday, rain or shine, head to the Kingston Farmer’s Market located in the Uptown District. This is our favorite place to go for all things local (they boast a wide array of regional vendors, including all the standard farmer’s market fare plus local syrup, samosas, and everything in between). It’s also one of our favorite stops for live music and people watching. KingstonFarmersMarket.org

Headstone Gallery

This gallery is one of our go-to spots to check out contemporary art exhibitions. The 1,200 sq ft space was created by artists Lauren Aitken and Chase Folsom and often features local pop-up shops and ceramics as well. HeadstoneGalleryNY.com

Assembly

A guide to Kingston would not be complete without including this local staple. Located in the top floor of a former Catholic school built in 1912, this event venue has become a cultural hot spot for all sorts of shows and community events, from live music to comedy. AssemblyKingston.com

WALK

Scenic view of a trail at Sojourner Truth State Park along the Hudson River in Kingston
Trail at Sojourner Truth State Park. (Photo: New York State)

Kingston Point Rail Trail

Take in all the local nature with our favorite ways to see Kingston. This mostly flat 1.8 mile trail provides a fantastic pedestrian and bicycle safe route, from the Rondout waterfront to Midtown Kingston, along with some picture perfect waterfront views to boot. It takes about 30 minutes to an hour to complete. KingstonGreenline.org/kingstonpointrailtrail

Sojourner Truth State Park

It’s hard to say Sojourner Truth State Park is a hidden gem when it spans about 520 acres, but we do consider this new sprawling State Park within the city of Kingston one of the Hudson Valley’s most highly underrated treasures. With 150-foot limestone cliffs, wetlands, and scenic views of the Hudson River Sojourner Truth State Park is a must-see on our guide. Pro tip: During summertime, get to the park early in the day to get the best parking, the lot fills up quickly on nice days. Parks.NY.gov/visit/state-parks/sojourner-truth-state-park

COFFEE + SMALL BITES

People enjoying snacks and conversation at Rough Draft in Kingston, New York
Enjoying some good snacks and conversation at Rough Draft. (Photo: Keap)

Rough Draft

Part book store, part venue, part coffee shop and part bar… is there anything Rough Draft can’t do? This place is truly one of kind and one of our favorite spots to grab a cup of coffee (they make a mean latte and some fun seasonal drinks) or beer, make a new friend, or find a good book to cozy up with. Rough Draft is located at Kingston’s four corners and has a sweet outdoor patio where you can take in the historic views. Plus, there is always at least one cute dog waiting to be pet outside. RoughDraftNY.com

Sweet Maresa’s

This bakery is absolutely incredible, and not just as a vegan option. It's our favorite bakery in town, even as non-vegans. Their specialty is their macarons and they come in plenty of intriguing flavors, but everything Sweet Maresa's makes is delicious. Our favorites are the marzipan cookie and the crumb cake. SweetMaresas.com

DRINKS

Woman standing at a bar opening bottle of wine
Cheers to the team at Brunette! (Photo: Keap)

Brunette

This cozy wine bar offers an assortment of natural wines, delicious small plates and bar snacks in the historic waterfront district of Kingston. BrunetteWineBar.com

West Kill Supply (Kingston Taproom)

West Kill is a small batch craft brewery in the Catskills, with it’s taproom located here in Kingston. We love to stop in to try out tasty local beers in their laid back and rustic space. The backyard is very dog and child friendly! WestKillBrewing.com

EAT

Six people seated around a table with food and open wine bottles
A Keap holiday dinner at Chleo's. (Photo: Keap)

Chleo

The exquisite tapas style plates, excellent wine selection, and beautifully cozy space make this a perfect spot for a date or catching up with friends. We appreciate their focus on local and seasonal ingredients. Note: On weekends, it can get busy and they don’t take reservations so we recommend arriving on the early side. ChleoVin.com

Kingston Bread + Bar

This place is known for their sourdough, pastries and coffee, and is also one of our go-to lunch spots. If you stop by, make sure to try the sourdough baguette. Kingstonbread.com

SHOP

A table and shelves filled with merchandise at Folk Refillery and Supply
One of our favorite shops in town, Folk Refillery & Supply. (Photo: Folk Refillery & Supply)

FØLK Refillery & Supply

Stop by Folk Refillery & Supply for eco-conscious and locally sourced goods for low impact living. This is the perfect shop to pick up some seriously cool local artisan gifts while you’re in town. FolkRefilleryandSupply.com

Kingston Social

An Italian style cafe in Kingston! This place is a gift store, Italian coffee and pastry shop, and hosts a selection of rotating art exhibits. The space is bright and welcoming and there’s something for everyone here. KingstonSocialNY.com

The Department of Things

This print shop and gift store located in the historic Rondout district of Kingston is a great place to find a present for any creatively inclined loved-ones, or just marvel at all of the neat treasure trove of stationary and art supplies they have for sale. Print making classes and community events are also hosted in the space. Say hi to friendly owner Kristin for us!
TheDepartmentofThings.com