Getting Lost Upstate
A trip through the Hudson Valley
I spent most of the eighteen years I lived in my hometown trying to get out.
Filled with overgrown trees, failing businesses, and local football leagues, there was nothing for me there. I was bored and misplaced. I wanted to go somewhere that didn’t require a car; somewhere where there was always something happening. I wanted it so much I printed out directions from MapQuest for how to get to bigger cities and hung them around my room. I needed more. I certainly never heeded thoughts to the contrary, including those from my Bard Bridge Program professors in high school: “Big cities are great, but sometimes creativity requires quiet.”
This idea was lost on me in college, too, where I was so entrenched in Manhattan it was practically an extension of my body. When I moved back briefly in 2020 during graduate school, the isolation still felt more stressful than soothing. But recently, all I’ve wanted are the sleepy nooks and crannies of the Hudson Valley. So I’ve been making lots of trips.
Here’s your guide to some of my favorite places, plus a few apple-themed must-haves to remember a fall day upstate.
High Falls / Stone Ridge / Kerhonkson
Too small to be towns, yet big enough to have names, these three census-designated places are just down the road from where I grew up. The drive offers gorgeous views of mature trees, historic stone houses, and lots of farmland. It’s definitely more rural than Stars Hollow, but the same vibes are there. Hasbrouck House could certainly give the Dragonfly Inn a run for its money with its renovations making it one of the world’s most romantic boutique hotels.
Putter about recently opened Blue Heron Books to discover your next great read or a rare find among their new and used selection. Have some surprisingly good sushi at Momiji or an ice cream treat at Cherries, which is a 1950’s drive-up style cafe. There’s also Minnewaska State Park for anyone looking for a hiking trail to clear their head.
The most essential fall activity, of course, is spending the day roaming through an apple orchard, picking your own. Kelder’s Farm has fields of fun for everyone, offering hayrides, wine slushies, and the world’s largest garden gnome among other games and entertainment.
Rhinebeck
This village is just across the Hudson River and a stone’s throw from Bard College’s campus. Home to antiques galore, it’s a lovely place to go if you’re looking for something special for your place. Stay right in town at the Beekman Arms Inn to experience it all, which has a tap room restaurant. Listed as a Historic Hotel of America, it claims to be the longest continuously running hotel in the country.
There’s tons to explore here, including the Farmer’s Market on Sundays through December and Rhinebeck Wine & Liquor for all of your local imbibing delights. Oblong Books has tons of options for reading, and Samuel’s Sweet Shop is sure to satisfy sugar cravings (it might offer a celebrity sighting, seeing as its co-owned by Jeffrey Dean Morgan, Hilarie Burton, and Paul Rudd). For the outdoorsy types, take a quick drive to nearby Red Hook for a stroll in Poet’s Walk Park, which has offered solace and inspiration to folks since 1850.
Duchess County is also wonderful for wine tasting. My favorite vineyard is Milea Estate Winery, just fifteen minutes from downtown Rhinebeck. They offer $25 tastings at their farm house alongside a menu of seasonal culinary delights and a gorgeous view. I’ll cheers to that!
Woodstock / Mount Tremper / Phoenicia
Emerson Resort & Spa offers a tranquil escape in the heart of the Catskill Mountains, plus a variety of unique shops selling everything from homemade jam to Jellycats. It’s the perfect spot to stay if you really want to reconnect with nature and disconnect from the world. There’s a pool on property in summer and a hot tub as temperatures drop.
Drive down the road to see the Ashokan Reservoir, which serves as a water source for New York City. It was built from 1907 to 1915, and required residents of twelve communities as well as thousands of acres of farmland to relocate in order to flood the area out. Even cemeteries had to find a different final resting place! It’s an interesting history lesson and a beautiful view of the sunset.
You’d be remiss not to stop by Woodstock, too, for hippie sightings and other interesting finds. For the record, this isn’t where the festival was (head out to Bethel Woods for that), but it’s still an artsy, music-loving town. Tinker Street has a number of photography galleries with rotating exhibits, and The Golden Notebook has welcomed readers since 1978. For a unique souvenir, make your own candle at Candlestock. I would also highly recommend a quick lunch at Oriole 9.
Saugerties
Last but least, a beautiful little village right along the Hudson River. Saugerties is sleepy and charming in equal measure, offering both cute stores to browse and beautiful grounds to hike. Diamond Mills Hotel provides luxury along the water as well as a farm to table restaurant and spa.
Skip the Instagram Influencer-approved eateries and instead start your day with a big breakfast at Village Diner. It may look unassuming, but it’s got the best corn beef hash and milkshakes. Another area favorite is Dallas Hot Weiners if you’re in the mood for a juicy hot dog.
When you’re after sweets, look no further than Krause’s Chocolates. The candy store has been around for nearly 100 years and makes delicious creams, chewy caramels, and divine chocolate-covered graham crackers. Montano’s Shoe Store provides a personalized fitting experience while offering the trendiest brands. And of course pop into Inquiring Minds Bookstore to check out their dog wall of fame and record selection.
Rachel’s Weekly Recs:
Once you’ve picked those apples, turn them into apple muffins! I’ve used this recipe from Sally’s Baking Addiction for years and it never disappoints. Choose at least two different kinds of apples to include, and don’t forget the icing drizzle on top.
If you’re looking for a perfect fall cocktail to go with those muffins, try some Applejack from the Hudson Valley Distillers. Popular in the Colonial era, this boozy drink is made from aging apple juice in oak barrels.
The best smelling thing I’ve purchased recently is this Caramel Apple candle from Cam’s Candles. It truly smells exactly like the real thing, which warrants the hefty price tag. One warning, though: burning before bed will definitely make you crave sweets.
I am from lower westchester but have spent a lot of this fall escaping home to see more trees as well!