Housed in an 1870s storefront, Ship to Shore is the longest-running restaurant on Kingston's historic Rondout waterfront. Chef-owner Samir Hrichi serves a globally inspired menu—crisp salads, sushi-grade tuna, fresh-caught seafood, hearty pastas, and a standout 24-ounce steak. With the marina steps away and river views all around, it's a reliably memorable spot.

Set inside a converted schoolhouse in Kingston's historic Uptown district, Assembly has quickly become the Hudson Valley's go-to spot for live music. The intimate space—capacity around 450—pairs top-tier sound with touring national acts and local favorites spanning folk, rock, Afrobeat, and beyond. DJ nights, art shows, and community events round out the calendar.

Set in a former antiques shop on Broadway in Kingston's Rondout district, Rosie General is part bakery, part Italian-meets-Jewish deli, part provisions market. Chef Anthony Sasso bakes daily bread and bagels, cures pastrami and headcheese, and jars house pickles and condiments, joined by the rest of the Sasso family behind the counter. Grab a stool at the marble counter or a shelf of local goods to go; either way, it's a Kingston favorite worth the stop.

Sorry, Charlie is a laid-back neighborhood bar and pizzeria cooking up pies that split the difference between New York and Detroit style, with the crowd-favorite Hot Debbie piling on whipped ricotta, pepperoni, hot honey, and banana peppers. Round it out with potato beignets, a pimento cheese dip, and inventive cocktails, and it's easy to see why this no-frills spot has become a local favorite.

For over 30 years, Hudson River Cruises has sailed the Rip Van Winkle II from Kingston's Rondout waterfront. Hop aboard for a 90-minute narrated tour past historic lighthouses and grand riverside estates, with drinks and light bites available on deck. Sunset cruises, live music nights, and private charters round out the options.

The Empire State Trail runs right through Kingston, putting scenic riding within easy reach. Head south along the Hudson Valley Greenway for river views through the historic Rondout waterfront, or cross the Kingston-Rhinecliff Bridge toward Rhinebeck and Tivoli. Paved paths and quiet country roads suit casual riders, while longer stretches toward New Paltz offer a full day's adventure for the more ambitious.

Sojourner Truth State Park sits along the Hudson River in Kingston, built on the site of a former industrial quarry. Its centerpiece is Lake Sophia, a spring-fed swimming hole with striking turquoise water, ringed by limestone cliffs and named for Sojourner Truth's daughter. With trails, picnic spots, and river views nearby, it's one of the Hudson Valley's newest, and coolest, summer destinations.

Opened in 1920, Hasbrouck Park was Kingston's first official downtown park and remains one of its largest at 45 acres. It's a natural pick for families, with a playground, softball field, and easy walking trails for little legs to explore. History buffs will appreciate the Stone Building, a 1919 quarry structure now used for events and recreation programs, while a pavilion with Hudson River views offers the perfect spot for a family picnic.

Rising 260 feet in two dramatic tiers, Kaaterskill Falls is one of the tallest waterfalls in New York. An easy gravel path leads to an overlook platform with sweeping mountain views, while a steeper trail with hundreds of steps takes more adventurous hikers down to the base for an up-close look at the cascade. Just stick to the marked trails, since the rocks are slick and the drop-offs are real, but the payoff is one of the Catskills' most iconic sights.