Spending a perfect day in a sexy, resurgent town.

by Jack Rico

Kingston, New York is one of the first places I visited when I moved Upstate more than a decade ago. What struck me immediately was its history and old-world charm. Right now, it’s experiencing something of a renaissance marked by new luxury hotels, quaint cafés, high-end restaurants and sprawling resorts which have made it an ideal getaway anytime of the year. 

Here’s how I spend an idyllic 24 hours on a Saturday in the Kingston I love.

10:15 a.m.

I start my morning in Uptown Kingston at this indelibly charming place I discovered a few years ago called Rough Draft Bar & Books. It’s a café, bar and bookstore that looks like the set of a love story—clearly part of its allure. As a journalist, my love for books is real and whenever I walk in here, the enchanting atmosphere alone beckons me to crack open a classic tome as I sip on a frothy cappuccino. People all around me are immersed in their reading, others engaging in apparent deep conversations. It’s a vibe I always want to live in.

11:22 a.m.

Just outside the bookstore is The Four Corners, a historic intersection where the stone houses on all four corners were built prior to the Revolutionary War. I  take my time absorbing it, take photographs and muse how these blocks appear almost untouched by modern times. Now there are shops just around the corner, such as Exit Nineteen, an eclectic store with unique furniture and gifts. My wife is a big fan and never leaves here empty handed. Nearby is the Old Dutch Church, a landmark structure and cemetery that has a prayer board where they have colorful slips of paper and pencils and encourage one and all to stop and “Take a Prayer, Leave a Prayer.” It’s a nice way to stop—if only for a moment—and just reflect. 

1:05 p.m.

I meet up with my wife at the Rondout, Kingston’s downtown waterfront, for lunch at one of our favorite eateries, Ole Savannah Southern Table & Bar. This place is right on the Hudson River housed in a former 1880s steamboat building and carries with it a tasty Southern menu. We have a seasonal special appetizer of Tuna Poke Oysters made with ponzu sauce and tobiko. We can’t get enough of them and order seconds of what we fondly call, “oysters on crack!” (they were that good).

2:30 p.m.

Following our delicious meal, we decide to check out an exhibit at the West Strand Art Gallery. The exhibit is called Metaphors featuring a collection of artists addressing issues of racial and gender boundaries through their art. We are intrigued by the paintings by Rodríguez Colero which are quite striking in their combination of classical and urban influences.  

Kingston New York

4:02 p.m.

We now have reservations for a chartered sail with close friends. There are quite a few marinas to choose from, but we usually go with Captain Dan’s catamaran from Hudson Sailing. Getting on a catamaran on a summer day, a chilled sangria on hand, sun and river refreshing the skin…three hours have never flown by so quickly. It’s no wonder why I’m always taken aback by the majestic beauty of the Catskills mountains from the river. It has truly become one of the great summer joys of living in this corner of the planet.

7:05 p.m.

Following the relaxing river excursion, we head over to Hutton Brickyards, a one-time brick manufacturing plant now turned into a luxury hotel/resort, for dinner at the River Pavilion, where an open-air restaurant with wood-burning ovens awaits us. As we sit down with the humbling panoramas of the Hudson in our sights, the place is buzzing with beautiful people and great, vibey music. It’s seriously mountains chic at its best and the delicious food is inspired by the region’s own harvest. If we didn’t already live nearby, I’d love to wake up in one of their cabins overlooking an unobstructed view of the river in all its glory. 

Sunday, 7:10 A.M.

Getting an early start this morning as today is beach day! First stop is Dolce in Uptown for a to-go order of coffees and Nutella crepes as we head over to Kingston Point Beach, the perfect spot for a lazy Sunday brunch. Being early is key, before it gets too crowded. As the time passes by, I find myself thinking 24 hours just isn’t enough time to be in Kingston. Can we make it longer, please?

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