Kingston Weekender

Full disclosure: this author was born and bred in Kingston, though I spent a great many years trying to get as far away from this town as possible. When I was younger and grumpier, the annual Burning of Kingston reenactment seemed proof enough that the only thing my hometown had to offer the world was a celebration of its own destruction. I’ve since changed my tune, as there is now plenty to enjoy in Kingston. This is a ride that is as much about the destination as it is about the journey.

Day 1: Poughkeepsie >> Kingston via New Paltz

Start in New Paltz. New Paltz is a charming little town on the banks of the Esposus Creek, and the first town you’ll hit coming from the Poughkeepsie station. Grab a burger and a beer at Clemson Bros. Brewery. Grab some knowledge at Barner Books. Get your gear in order at Bicycle Depot. 

Stop for the sights (and the selfies). There are good ones to be had on these trails. Walkway Over The Hudson is a universal crowd pleaser. The Rosendale Trestle offers another grand photo op. Somewhere about three quarters of the way to Kingston are cement kiln ruins that make good bike selfie backdrops. I can’t for the life of me recall exactly where they are, but Google satellite view gives me hope that they are somewhere in this general area.

Stay Uptown. Other neighborhoods that may look appealing in your search are Midtown and the Rondout. I recommend staying Uptown since it will put most things within easy walking distance. Uptown Kingston is also known as the “Stockade District”, a rebrand that followed the exodus of NYCers to upstate. Locals call them “citidiots”; my mother more affectionately refers to them as “The Brooklyn People”. Name calling aside, you’ll find plenty of good grub here.

Dine at Le Canard Enchaine. There are no shortage of great new restaurants in Kingston, but I’m going to shamelessly plug the one fine dining experience that predates the arrival of The Brooklyn People. It’s also a fun dining experience. Longtime owner and sometime chef Jean-Jacques is as gregarious a Frenchman you’ll find on this side of the Rhine. This place has been around as long as I can remember, and as a lifelong Francophile I can attest it is damn good. 

Drink at Keegan Ales. Another hometown favorite that predates (most) of The Brooklyn People. Order anything on tap, you can’t go wrong. For more Brooklyn fare, check out Kingston Standard Brewing Co. Whatever you do though, please don’t drink and bike... 

Day 2: Kingston >> Poughkeepsie via New Paltz

Recover Uptown. Start your day with the best breakfast sandwich in town and a pain au chocolate at Kingston Bread + Bar, paired with a flat white from Rough Draft Bar & Books. If you hang around through lunch, Diego’s Taqueria is a safe bet for quick eats. At some point find your way into Outdated, if not for the food and drink, then at least to peruse the many cabinets of curiosities that line the walls. Above all else, treat yourself to the Hudson Valley’s best cheese danish and late-80s restaurant interior design glam at Deising’s Bakery. 

Stock up Uptown (and Midtown) too. If you go to only one store in Kingston, please, do yourself a favor and head over to Zaborski Emporium. The place is an experience. I’ll let their Instagram account do the talking (or read this article). If, on the other hand, the Brooklyn Person is simply too strong in you, check out Hamilton & Adams for expensive t-shirts, beard oil, and whatever other lumbersexual fetishes you desire. You may also rejoice in Rhino Records for, to paraphrase my favorite New Yorker cartoon, the expense and inconvenience of vinyl—especially on a bike!. Finally, if you actually need something more useful for your bike trip, Utility Bicycle Works has you covered. 

History buffs of the world delight! Kingston’s roots go back quite some time, the remnants of which you’ll find readily Uptown. Some highlights include: the Senate House, which was home to New York State’s first government; the Old Dutch Church, built in the 1600s (!!!) and burial site of the OG George Clinton (i.e. of the Revolution, not of the P-Funk); and the only block in the United States where the buildings on all four corners pre-date the Revolution (Crown St. and John St., right where Rough Draft Bar & Books is).   

Extend your stay. There’s plenty more to keep you occupied in Kingston and beyond to make your weekender longer. You could bike down to the Rondout, along the newly completed Kingston Point Rail Trail, and (weather permitting) catch some sun at Kingston Point Beach. If you can find a car to haul your bike, you could also tack on a ride through the very scenic Ashokan Rail Trail (technically you can pedal there, but bike on Route 28 at your peril...). Closer to New Paltz is the equally scenic River-to-Ridge Trail. If you’re feeling especially ambitious, take that trail straight up to the gates of Mohonk Mountain Preserve and spend a night in the astonishingly Old World Mohonk Mountain House. Just note, you may want to walk your bike since it’s a hell of a climb to pedal!

Trails

• Walkway Over The Hudson
• Hudson Valley Rail Trail
• Wallkill Valley Rail Trail
• O&W Rail Trail