Rhinebeck, NY
When I was a kid, my grandfather had a house in Upstate New York in the town of Red Hook. Every summer, we would drive winding back roads to make the trip to ”the country” to spend a few weeks. I have fond memories of swimming and boating in the lake, rummaging through the antique barns, and going to the Duchess County Fair to buy milkshakes, watch the potbelly pig races, and, if you were lucky, see a cow giving birth in one of the barn stalls. Our grandfather would bring my sister, my cousins, and me to Saratoga race track and give us each exactly $11 (one for each race) to spend betting on the horses. We would sit in the picnic area eating peanut butter jelly sandwiches, pouring over the program and debating whether we should pocket our winnings or place a boxed trifecta in the next race.
As an adult, I still make the trip back upstate to spend some time swimming in the lakes, taking in the beauty of the country, and watching fireflies. It’s still a great place to relax and regroup. You’ll find many New Yorkers coming here to take a break from the chaos of the city as it’s just a short metro ride away. You can catch the Amtrak straight from Penn Station and the trip will take you on a stunning route along the Hudson River so be sure to grab a window seat on the left-hand side.
Stay
The Historic Beekman Arms Hotel which dates back to the 1700s is conveniently located in downtown Rhinebeck. This summer my family rented an Airbnb in nearby Rhinecliff where the rates were a little less expensive. The house was a short walk from the train station and the Hudson river which has amazing views, especially during sunset.
Downtown Rhinebeck
It’s fun to walk around the picturesque and historical downtown area of Rhinebeck and to pop into the shops and specialty stores. The Krog is a good place to get a local beer. Dining options include Fosters: A casual dining spot with burgers, fries, etc. The Terrapin offers a unique upscale dining experience in a renovated former Church dating back to 1825. The Amsterdam: farm to table dining from husband and wife owners. Bread Alone: Freshly baked goods. Stewart’s Shop: get a hand-packed pint. Or six.
Bard College
Check out the grounds of the beautiful Bard College campus in Annandale-on-Hudson. They have a gorgeous Garden area overlooking the Hudson River. Throughout the year they put on public events, concerts, and performances. Keep an eye out for the pump ” that don’t work cuz the vandals took the handles” from Bob Dylan Subterranean Homesick Blues.
Summertime
Dutchess County is home to some gorgeous pristine lakes that are perfect for swang on a hot summer day. Twin Lakes in Elizaville has a beautiful public beach area with picnic tables and grassy areas for lounging. Taconic State Park is another good place to swim with a kitty pool tar pit and a larger lake with a dock for adults. Omega Institute is a private facility that has a beautiful beach area, dock, and boats, and canoes that you can take out on the lake.
Take advantage of the many nearby Farms and go strawberry or blueberry picking. Grab a pint to fill up at the entrance and pay on your way out.
The Dutchess County Fair is as authentic as they get. Carnival rides and games, country music entertainment, livestock shows, fair food, and the Horticultural exhibits are some of the highlights of this week’s long event. Be sure to check out the potbelly pig races we’re “Tyrone the Terrible” is sure to amaze you.
Every summer, Bard College is home to the Spiegeltent which is traditionally a large traveling tent, constructed from wood and canvas and decorated with mirrors and stained glass, intended as an entertainment venue. They held event every weekend open to the public where you can come and dance the night away under the tent lights. DJs and performers from all over have come here to perform including Andrew Andrew, John Cameron, and Alan Cumming.
Fall
Every fall, Rokeby Farms hosts a Sinterklass parade festival. This is a festival of lights featuring intricately crafted two-story puppets. The Sinterklaas tradition comes from the Netherlands and was brought by Dutch settlers who arrived in Rhinebeck over 300 years ago. During this parade,” children are transformed into Kings and Queens and honored as the bringers of the light at the darkest time of year.” All are welcome to attend and participate in this parade and in the months leading up to it, volunteers gather at Rokeby farm to lend their artistic talents to working on the puppets for the parade.
