Upstate and Hudson Valley, New York
I am so happy I am spending time back in New York this Fall - especially around Upstate and Hudson Valley. It is so charming and lovely in the Fall months, so this seems a good time to revisit some of my favorite towns.
Shop some of my travel essentials / my LTK / my children’s travel book / Plannin hotel recommendations / Travel Aunties
Visit Upstate NY Tourism and Hudson Valley Tourism
I have always loved driving upstate, or hopping the train to Hudson Valley, though apparently many of you do too as tourist flock to this area come Autumn, and many New Yorkers moved out of the city to the space up here for some literal fresh air. There are so many new, cool smalls businesses, restaurants, breweries and more. So where to start? Let’s review some of my favorite stops on both sides of the river - the most desirable villages, towns, and cities that may already be on your radar, along with some that may not be. Fortunately the types of living that the region is known for — sleepy walkable villages, small industrial river towns, and bucolic rural escapes — are plentiful. And check out Escape Brooklyn for more
Tarrytown, Cold Spring, Sleepy Hollow: The closest train stop in the valley from NYC, and all next to each other. Tarrytown and Sleepy Hollow are side by side, with Cold Spring just a couple more train stops north. Tarrytown has an upscale colorful vibe. Walking along the shopping district, you’ll also find trendy boutiques, galleries, and numerous antique shops. Formerly known as North Tarrytown, Sleepy Hollow is a mecca for Washington Irving fans. The town has several historic sites plus a nearby state park. Sleepy Hollow Cemetery is the final resting place of writer Washington Irving and several famous figures including Andrew Carnegie, Walter Chrysler, Elizabeth Arden, and Leona Helmsley. Its fabulous for halloween for obvious reasons too.
Nyack: Rockland has the reputation of being more bohemian than nearby Westchester — especially Nyack, which has been home to writers, actors, and artists for generations (the most famous being Edward Hopper). On a given night at a village bar, you might find a magazine illustrator for Rolling Stone in conversation with a singer and the mayor. For a large Italianate home on a leafy lot along the river, look toward Upper Nyack, and for a colorful Victorian on a quiet, dead end street, you’ll want to be in South Nyack. There is some stylistic overlap.
Rhinebeck, Germantown: The village of Rhinebeck has long been seducing city dwellers into abandoning busy urban lives, even if just for the weekend. It is home to the oldest Inn in America — Beekman Arms — where grand figures from George Washington to Oprah Winfrey have been lulled to sleep. Trotting along its main streets (Montgomery, Market, and Mill) past an old-fashioned-style candy shop, a 50-year-old movie theater, and some of the best restaurants in the Valley, it is easy to understand the appeal. Celebs like Paul. Rudd and Jeffrey Dean Morgan live here, and even rescued a local candy shop ( Samuel’s Sweet Shop)! Germantown sits near the border of Dutchess and Columbia counties and is also one of the best places to live in the Hudson Valley. Historically, it is a farming community founded by Palatine German immigrants. The rolling farmland and farmhouses surround a central village with an updated old grocer, Otto’s, where you can get a breakfast sandwich on site and then pick up local produce and specialty groceries like Roberta’s frozen pizzas or Black Seed bagels.
Beacon: Situated right on the mighty Hudson River, Beacon boasts bucolic beauty, hiking trails galore, a thriving art scene, small town whimsy, urban ruins, plenty of terrific food and drink, and a castle
Kingston: Despite Kingston’s well-established reputation as the cool capital of the Hudson Valley, it still keeps its charm. We were surprised to find that in some ways he is right. For a mid-Hudson city with so much personality — the old maritime feel of the Rondout, the historic appeal and nighttime bustle of Uptown
Woodstock, Saugerties: To assume that Woodstock is only notable for its namesake 1969 music festival would be a major blunder—the festivities weren’t even held within city limits. In reality, Woodstock is a charming little Catskills oasis where fewer than 6,000 residents prop up an art, religion, music, and theater scene worthy of national attention.
Hudson: The Brooklyn of Hudson Valley, All of our small cities have beautiful architecture along a main corridor, but the historic row houses along Hudson’s Warren Street seem taller, older, grander, or somehow just…more. Perhaps it is because they are so beautifully preserved or because Hudson, far from Manhattan, has had to exist on its own terms. Echoes of the past — the whalers, the iron and brick workers, generations of migrants, and Hudson River School painters — mingle with the chatter of the designers, chefs, farmers, and tastemakers who drive its energy today.
Catskill: Right across the river from Hudson, also with a wonderful downtown with good restaurants and an artist’s flair.