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For city-dwellers looking for a breath of fresh air, there’s nothing like heading upstate. As a New York City girl, I’ll admit I was dubious about an upstate weekend getaway; The mysteries of the Catskills can feel overwhelming to someone who is used to the hustle and bustle of city life.

But, readers, I’m here to tell you: There is NOTHING like an adventure to Upstate New York. From mountain climbing in Bearsville to staying in a 17th-century cottage in New York’s original state capital, my upstate adventure was filled to the brim with things to do. New Paltz to Bearsville, Woodstock to Kingston, Beacon and beyond, stick with me as I walk you through my top 10 things to do in the Catskills.

1. Nature Walk Through Mohonk Preserve (New Paltz)

Mohonk Preserve
Mohonk Preserve. Photo by Clay Banks on Unsplash

Welcome to the largest non-profit state preserve in New York State (and with almost 500 public and private parks in New York, that’s no small feat!). Mohonk Preserve protects over 7,000 acres of forests, fields, streams, rivers, mountain ridges, and other mystically unique environments.

What does this varied terrain mean, readers? For the adventurous traveler, this means hiking, biking, climbing, running, bird-watching, horseback riding, and anything else your outdoorsy heart desires. Preserve lands are open from sunrise to sunset, so you have all day long to wander and explore. 

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While you’re there, don’t forget to check out Mohonk Mountain House. Founded in 1879, this historic Victorian castle sits tucked away on a cliffside in Mohonk, overlooking an ever-ominous glacial lake. Check out this historic landmark for an added (and spooky?) Mohonk bonus. 

**Fun Fact** – Mohonk Mountain House is rumored to be the inspiration behind Stephen King’s horror classic, The Shining!

2. Grab Breakfast at Main Street Bistro (New Paltz)

Main Street Bistro menu. Photo by Aurie Ceylon
Main Street Bistro menu. Photo by Aurie Ceylon

If you’ve never been to New Paltz, you’re missing out on one of New York State’s most adorably underrated small towns. While it’s only a 90-minute drive from New York City, this incorporated village is located deep in the Shawangunk Mountains, and it will give you the rustic and woodsy feels you’ve been craving. With tiny storefronts, used bookstores, and pizza parlors on every corner, it’s easy to feel overwhelmed by its small but jam-packed main street. 

However, readers, you cannot overlook the vintage and classically creative charm of Main Street Bistro. Not sure where to find it? That’s easy, just follow the crowd of eager weekend brunchers, as Main Street Bistro almost always has a short wait on busy mornings.

Chock full of young families, tourists, and seasoned New Paltz residents, the diner is almost overstimulating with its colorful bumper stickers, vintage 1950s booths, and even saloon-style doors for the restrooms and kitchen.

For the people-watchers, grabbing a seat at the counter is an absolute necessity. Seats are cozy and intimate, making it feel like the diner is truly one big community breakfast. 

Get the hash scramble. Trust me. 

3. Hike Overlook Mountain (Bearsville)

Overlook Mountain Trail hike (view from fire tower). Photo by Aurie Ceylon
Overlook Mountain Trail hike (view from fire tower). Photo by Aurie Ceylon

For the adventurous traveler, look no further than the extremely steep and wildly rewarding Overlook Mountain trail. But be warned, readers: This trek is no easy feat. With steep cliffs, rocky edges, and an ominous gravel road, it’s easy to lose your way (or your footing!).

With a trail length of 4.6 miles and a maximum elevation of 1,397 feet, the Overlook Mountain trail offers physical challenges, scenic views, and a big payoff if you reach the very top. At the height of the trail, take in panoramic views of the Hudson River, the neighboring town of Woodstock, and the vast and seemingly endless wilderness of the central Catskill Mountains. 

**Bonus** – For those unafraid of heights, accept your final challenge and climb the ever-so-shaky Overlook Mountain trail fire tower. This unsteady 60-foot thrill ride offers incredible (and windy) views that extend all the way to the Berkshires! 

4. Visit a Mountainside Monastery (Woodstock)

KTD Monastery. Photo by Aurie Ceylon
KTD Monastery. Photo by Aurie Ceylon

Yes, a monastery. Yes, it’s on a mountain. Overlook Mountain, to be exact!

Just across from the base of the ambitious Overlook Mountain trail is the Karma Triyana Dharmachakra (KTD) Tibetan Buddhist Monastery. KTD offers a respite for weary wanderers, a meditative space for those in need, and a public access space for curious tourists.

Built in the traditional Tibetan style, the walls are adorned with red, green, and gold fabrics, statues, and hundreds of candles. Silent Buddhist Monks go about their daily routines while visitors are welcome to stroll, meditate, pray, and explore. 

5. Explore Overlook Mountain House (Bearsville)

Overlook Mountain House. Photo by Aurie Ceylon
Overlook Mountain House. Photo by Aurie Ceylon

Ready for a spooky adventure? On your way to the top of the Overlook Mountain trail, you will notice what appears to be an abandoned mansion. Look closer and you will find yourself face to face with the creepy-yet-historic ruins of Overlook Mountain House.

Located near the summit of the trail and sitting on a very daunting cliffside, this historic hotel has over a century of secrets. Built in the 1830s, the luxury hotel was originally created to draw in wealthy socialites looking for a luxury weekend escape.

However, the hotel could not stay afloat and shut its doors after a few years. The hotel was later sold, rebranded, and reopened in 1871. But, rather, unfortunately (and mysteriously) – the hotel burned down in 1875.

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I know what you’re thinking: What a creepy story! – But the story doesn’t end there, readers. The hotel was later sold, rebuilt, and reopened for a second time in the late 1870s. 

But, get this – it burned down again in 1921! 

The hotel has been abandoned, shuttered, and dark ever since. It now sits as a historic landmark along the trail, and it is publicly accessible for all willing to traverse its scorched and historic steps. Walk by on your way to the top if you dare!

6. Stroll the Streets of Woodstock (Woodstock)

Woodstock Town Hall. Photo by Aurie Ceylon
Woodstock Town Hall. Photo by Aurie Ceylon

If you drive past the exit for Woodstock and you don’t stop by for a visit, you’re doing yourself a big disservice. This well-known yet overlooked town is the vibrant, colorful, charming, and quirky pit stop you didn’t know you needed.

Located in Ulster County (just a 5 minute drive from Overlook Mountain), Woodstock is famous for the Woodstock Festival, a cultural and generational explosion from the 1960s, and the Woodstock Film Festival, which brings in thousands of tourists and artists each year. It is also home to the Woodstock Jazz Festival, The Woodstock Guild, and the Woodstock Artists Association and Museum.

If those organizations and institutions aren’t enough to swallow up your Woodstock adventure time, you must walk up and down Tinker Street, which is always overstuffed with bakeries, cafes, music stores, novelty shops, and more. Stock up on fudge and tie-dye shirts before heading to your next adventure. 

(Make sure to stop by Yum Yum Noodle Bar for a cozy meal and quirky atmosphere)

7. Beacon Farmers Market (Beacon)

Downtown Beacon. Photo by Aurie Ceylon
Downtown Beacon. Photo by Aurie Ceylon

If you’ve ever wanted to star in your very own authentically wholesome 90s television series, this is your big chance. Well… not really, readers. But, I swear you’ll feel like the star of your own romantic comedy. Located in Dutchess County on the Hudson River is the quintessential quaint and artsy town you’ve been craving.

From stunning Victorian brick architecture to vibrant murals to small tea shops to barbecue joints to a massive mountain that seems to wrap around the town, there are so many ways to spend a day. Hike Mount Beacon (located at the edge of town in Mount Beacon Park!), then stroll the winding Main Street and take in the foliage, mountain views, and small town charm. 

While Beacon is basically the most beautiful town you’ll ever see, don’t get distracted, readers! We must focus on the top Beacon “to-do”: the Beacon Farmers Market. With the mission to create “a more just food system” within upstate New York communities, the farmers market has everything you could ever hope for.

From locally sourced lavender honey to soft cheeses to homemade tomato sauce to Ube rice krispies, this small but mighty market will keep you occupied (and snacking!) for hours. The market is located smack dab in the center of downtown Beacon, so there’s no way to stroll past it without taking in the sights, sounds, and smells. 

Catch it on weekends, rain or shine! 

8. Walk Through Kingston’s Historic District (Kingston)

Walk Through Kingston's Historic District. Photo by Aurie Ceylon
Walk Through Kingston’s Historic District. Photo by Aurie Ceylon

Get ready for a history overload, readers. Welcome to Kingston, New York’s original state capital! Kingston was the traditional home to the Esopus people. The Dutch settled in the early 1600s, then later incorporated the town as Kingston in 1652. It became the state capital of New York in 1777. 

**Fun Fact** Did you know that Kingston, NY is known as the town the British tried to burn? Why, you might ask? During the American Revolutionary War, the city was burned to the ground by the British, after the Battle of Saratoga, as punishment for aiding the Patriots. It was later rebuilt and, in the 19th century, became well known for its railroad and canal connections. 

Today, Kingston is a cobblestone walk through colonial New York. Take in the architecture of New York’s original state capital as you walk through its historic Stockade district. Make sure to stop for dinner at Hoffman House, a tavern located inside of a 17th century stone house and revolutionary lookout point!

9. Grab a Drink and a Read at Rough Draft Bar & Books (Kingston)

Rough Draft Bar & Books. Photo by Laura Kennedy on Unsplash
Rough Draft Bar & Books. Photo by Laura Kennedy on Unsplash

Bookstore? Bar? Cafe? What is this magical place? Readers, it’s all three. 

Located in Kingston’s historic “four corners” district, Rough Draft Bar & Books has cozy nooks and crannies for every reader, writer, drinker, chatter, and people-watcher. With a varied selection of wine, beer, coffee, espresso, and small bites, you can max n relax and take in the sights of downtown life.

The interior is both historic and industrial with wide wood plank floors, historic stone walls, and large warehouse windows. Events at Rough Draft range each week from trivia to concerts to game nights and more. 

Open from 8am-8pm, stay all day and live your literary (and boozy) dreams. 

10. Lose Your Mind at Glaze Over Donuts (Beacon)

Glaze Over Donuts. Photo by Aurie Ceylon
Glaze Over Donuts. Photo by Aurie Ceylon

Remember the vibrant and distractingly beautiful upstate town of Beacon? Well, readers, we can’t say goodbye to this picturesque hamlet without stopping by one of its most famous establishments: Glaze Over Donuts.

Located right on Main Street in an adorable pastel-painted cottage that looks like it belongs in Little Women, Glaze Over Donuts is the sweet treat you never knew you needed. From the moment you step over the threshold, you are overpowered by the warm and inviting aroma of fresh baked goods. And not just any goods…wildly customized doughnuts. Unlike most doughnut shops, where you choose from a selection of probably-stale options, Glaze Over makes your doughnuts on the spot. 

As in, you place the order, wait, and take home a fresh batch. 

As in, they’re warm

Is there anything better than a warm doughnut, readers? 

And the magic doesn’t stop there. Not only are the doughnuts fresh to order, but you can customize your sweets with an order form. Choose from toppings like cinnamon toast crunch, classic glaze, sprinkles, and even Fruity Pebbles (even this celiac traveler couldn’t resist a few glutenous bites). 

Worth every moment of anticipation. You can even watch them make the doughnuts.

Final Thoughts on the Catskills

Aurie in Upstate New York

While this New York traveler was wary at first, I have officially fallen madly in love with upstate New York. Sure, I’ve only seen a few small towns so far, but the foliage, food, adventures, and rich history has me desperate for my next trip into the Catskills and beyond. I returned from my trip with an armful of Ube rice krispies, soft sheep’s milk cheese, glazed doughnuts, and a ton of new historical curiosities to share. 

Whether it’s for a hike or a read, a spooky stroll or a farmers market, upstate New York has everything this wanderer needs for her next adventure. 

What are you waiting for?

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Author Bio: Aurie Ceylon is a writer, reader, and traveler from New York City. A quirky and self-proclaimed wanderer, Aurie writes detailed exploits of her adventures on her blog – hey, it’s aurie! Stick with this New York wanderer as she fills her heart – and stomach – in small towns across America.

Follow Aurie on Instagram to see more of her travel content! IG: @heyitsaurie

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