Ultimate Guide to the Catskills & Hudson Valley: The Perfect Weekend Getaway

Ultimate Guide to the Catskills & Hudson Valley: The Perfect Weekend Getaway

Your ultimate guide to Hudson Valley and the Catskills, aka the perfect weekend getaway from NYC. Three days exploring the region’s beautiful nature and quaint towns will have you recharged, relaxed, and ready to take on the world.

From the magnificence of the Kaaterskill Falls to the small-town charm of Woodstock (yes, that Woodstock), there’s something for everyone.

This guide walks you through a sample three-day itinerary for Hudson Valley and the Catskills, including what to do, where to eat, and how to get there. Basically, everything you need to know to have an incredible weekend away from the noise and lights of New York City.

Let’s get to it!

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PLANNING & LOGISTICS


ITINERARY

Since the Catskills and Hudson Valley comprise a large region and range of activities, there is no one-size-fits-all itinerary. Some people like hiking; others prefer vintage shopping or cultural sights. Itineraries also depend on where you decide to stay, which is why I included a bunch of different options in the What To Do section of this post.

The itinerary below is a sample based on my previous trips upstate. Feel free to customize your own! 

Tip: Save and star all the towns and places you want to visit on Google Maps for a big-picture view of where they’re located in relation to each other. This makes planning your route and itinerary 10x easier and faster.

FRIDAY: Leave earlier in the day, if possible, to beat both rush hour and upstate traffic (a lot of New Yorkers go upstate on the weekends, especially during fall). 

If you’re driving, it’ll take you a little under two hours to hit the town of Kingston. Eat lunch, browse the cute boutiques in uptown Kingston’s Stockade District, and soak in the maritime charm of downtown Kingston.

Then hop on over to the neighboring town of Woodstock, where you’ll find plenty of galleries, restaurants, and shops filled with tie-dye and bohemian goods. Grab dinner, check into your hotel, unwind, and get a good night’s sleep for some epic hikes the next day!

*If you’re leaving after work, you can eat dinner in Kingston and save Woodstock for another day.

SATURDAY: Nothing says “weekend getaway from NYC” like a beautiful hike upstate. Take the opportunity to bask in the sounds and sights of nature – which are far and few in between in the big city – by hiking the Kaaterskill Falls, Mount Tremper, or Overlook Mountain, to name a few options. 

Depending on the trail, your pace, and how early you start, you may be able to squeeze in two hikes. I’ve listed a bunch of options in the “What to Do” section later in this post; choose your favorite(s) and get excited!

Afterward, indulge in a delicious dinner and drinks at one of Saugerties’ farm-to-table restaurants. You earned it!

SUNDAY: Start the day off with a hearty breakfast in Phoenicia, which is home to the famous Phoenicia Diner and Sweet Sue’s (known for its pancakes). Take a short hike up the Tanbark Trail to burn off the calories from breakfast, then browse the hamlet’s tiny boutiques and pick up some candles or vintage clothing before you head back into the city. Or, if you skipped Woodstock on Friday, this is a good day to make up for it.

BEST TIME TO VISIT

Honestly, you can plan a weekend getaway to the Catskills for any time of year, but the “best” season depends on what you’re looking for.

SUMMER: Warm weather, ideal for hiking, fishing, and camping.

FALL: Cooler temperatures, but the fall colors are stunning and there’ll be fun activities such as pumpkin and apple picking. October is peak leaf-peeping season, and it’s also an excellent time for a hike. Personally, this is my favorite season to visit Hudson Valley and the Catskills.

WINTER: Great for snowy outdoor activities like skiing, snowboarding, and snowshoeing, but it will of course be cold.

SPRING: If I had to choose a “worst” season to visit the Catskills, it’s spring, aka “Mud Season.” Snowmelt means wet, muddy trails, more discomfort, and higher risks if you decide to go hiking.

HOW TO GET THERE

BY CAR: The Catskills are less than a half day’s drive from major northeastern cities like New York, Boston, and Philadelphia. For more information on which highway to take, check out the official Catskills tourism board website.This is the best option for exploring the Catskills, since you will need a car to drive between towns and to hiking trailheads. 

BY TRAIN: If you’re traveling from NYC, you can take the Metro-North or Amtrak upstate. They make multiple stops in the Hudson Valley and Catskills; you can find the full list of stops on their websites. However, once you arrive, you’ll have to take a taxi or rental car to your hotel.

BY BUS: Adirondack/Pine Hill Trailways offers bus service from New York’s Port Authority to dozens of towns in the eastern Catskills, including Kingston, Woodstock, and New Paltz. Shortline Bus will take you to the western Catskills.

Full list of Trailways stops

Full list of Shortline stops (put New York as your destination state and a list of towns Shortline services will pop up)

TOWNS TO VISIT

This is not a comprehensive list of every town in upstate New York – that would take a whole other blog post! – but it is an overview of some of the most notable. Pick and choose your favorites.

CATSKILL: Yes, there is actually a town called Catskill in the Catskills. A favorite of creatives, Catskill boasts numerous art galleries, studios, and museums.

KINGSTON: A cute little town nestled in the heart of Ulster County. Its uptown Stockade District is a mix of historic landmarks and contemporary dining and shopping; its downtown waterfront area is known for its galleries, eclectic shops, and bustling marinas.

PHOENICIA: Phoenicia is home to approximately 300 people, but what it lacks in population size it makes up for in natural wonder. It sits in the gateway to the Catskill Forest Preserve and offers two campgrounds (Black Bear and Sleepy Hollow), multiple hiking trails, and kayaking and tubing on Esopus Creek during summertime.

SAUGERTIES: Featured as one of Budget Travel Magazine’s “10 Coolest Small Towns in America” in 2009, Saugerties is down-to-earth, homey, and all-around charming. You’ll find plenty of indie shops, antique stores, and great restaurants. Fun fact: This is Jimmy Fallon’s hometown!

WOODSTOCK: Woodstock of Woodstock Festival fame is, as expected, a hippie haven with its plethora of galleries, eclectic shops, live music venues, and artsy, bohemian spirit.  It’s also one of the most popular weekend getaways for New Yorkers, so prepare yourself for more hustle and bustle than other towns upstate if you decide to visit.

WHERE TO STAY


Emerson Resort

EMERSON RESORT & SPA (Mt Tremper): A wonderful resort for those who want a modern, relaxing escape, the Emerson boasts both contemporary and rustic lodgings, a spa with an outdoor hot tub and steam room, an excellent restaurant, and the most charming hotel market/shopping area you’ll see. It’s located down the road from Phoenicia and is a short drive from multiple hiking trails.

I stayed here for a weekend girls’ trip and loved it! I even wrote a whole blog review about the Emerson, its amenities and service, and dining (including the one item you must order from their signature restaurant). Make sure to check it out if you’re thinking of staying here. I highly recommend this hotel for anyone who wants to feel pampered and relaxed.

HOTEL DYLAN (Woodstock): A colorful, retro boutique hotel with guestrooms named after 60s musicians or bands. Each room comes with its own Crosley record player. Other perks and amenities include hammocks, a ping-pong table, a seasonal pool with underwater speakers, and a ski lift-ticket discount at nearby mountains. Music lovers will be heaven! 

THINK BIG! A TINY HOUSE RESORT (South Cairo): If you thought “luxury” and “tiny house” don’t belong in the same sentence, you thought wrong. Think Big! is a tiny house vacation rental resort consisting of eight luxurious tiny houses that overlook Catskill Creek. The houses sleep 2-7 people; each comes fully equipped with a kitchen, full bathroom with flush toilet, heat/air conditioning, WiFi, TV and a private patio with a gas barbecue grill and fire pit. On-site amenities include a heated pool, waterfall, and kayaks. Livin’ large by livin’ small.

Hemlock Falls waterfall

HEMLOCK FALLS CAMPING (Parksville): More glamping than camping, Hemlock Falls is a great option for those who want to be in nature but also want to hold on to some creature comforts, like a flush toilet and mosquito netting. I’m not an outdoorsy person, but I stayed here for a weekend in May and enjoyed it.

There are only four campsites on 40 acres of private property, which means it’s nice and peaceful. Size and amenities vary slightly based on the campsite; you can find more information on each one on the Hemlock Falls website. We stayed at the Falls Site, which is the largest and only a 2-minute walk to Hemlock Falls (one of three waterfalls on the property). It had a covered wraparound deck, attached private half bath, picnic area with a fire pit, and an outdoor covered camp kitchen.  

Note: Hemlock Falls is only open from Memorial Day Weekend to mid-October each year. You can book via Airbnb.

WHAT TO DO


Note: Obviously you can’t fit all of these activities into one weekend, but I wanted to give you options depending on where you’ll be and what you enjoy doing. Mix and match to your heart’s content!

HIKING TRAILS

View from Tanbark Trail

  • Catskills Scenic Trail (26 miles): An easy trail that’s great for all ages. Popular recreational activities on this trail include hiking, biking, skiing (in the winter), and horseback riding with mountain and farmland views. Difficulty: Easy.
  • Kaaterskill Falls (1 mile to the base): One of the most stunning spots in the Catskills. The 260-foot, two-tiered waterfall is a favorite of Instagrammers and photographers; in the fall, when the colors are in full bloom, it literally looks like a painting. However, it is also one of the deadliest waterfalls in the world. I strongly advise against hiking Kaaterskill Falls in the late fall/winter seasons or after it’s been raining, because of how icy and slippery it gets. Due to accidents and deaths, the trail from the base of Kaaterskill Falls to the basin and to the top of Kaaterskill Falls is now closed. Some people still use it, but it is extremely dangerous. Nevertheless, it is worth a visit in the summer – just be careful! Difficulty: Moderate
  • Mount Tremper (6 miles): Located near Phoenicia, Mount Tremper is considered one of the more difficult hikes in the Catskills. Black bears are commonly seen at the top and there’s at least one confirmed rattlesnake den located close to the trail, so exercise caution when you’re navigating the mountain. It’s a steep climb, but it offers amazing views from the summit. Difficulty: Hard
  • Overlook Mountain (5 miles): This hike begins near Woodstock and ends at the top of a fire tower, where you’ll find sweeping 360-degree views of the Hudson River Valley. You’ll also find some cool 19th-century hotel ruins at the summit, which is an added bonus! Difficulty: Hard
  • Tanbark Trail (2 miles): The entrance to this trail is in Phoenicia. While it may not have the best views compared to some of the other hikes in the region, it’s a nice option for those who are short on time or not up for a hardcore workout but still want to get some physical activity in. Difficulty: Moderate

CATSKILL

  • Hudson River Skywalk (Activities): A scenic pedestrian path that connects Thomas Cole National Historic Site and Frederic Church’s Olana. You’ll cross the Rip Van Winkle Bridge, which runs over the Hudson River and connects Catskill with the neighboring town of Hudson, NY. There are three viewing decks along the Skywalk that boast amazing views of Hudson Valley.
  • Olana (Sights): Technically located near Hudson, not Catskill, but you can easily get here via the Hudson River Skywalk (see above). It’s a peaceful, scenic historic museum and property that was home to the Hudson River School artist Frederic Church. 
  • Shopping on Main Street (Shopping): A half mile of charming shops and boutiques, including Magpie Bookshop, a carefully curated used bookstore, and Village Common Mercantile, a lifestyle shop selling a mix of artisanal, handmade, and vintage goods.
  • Thomas Cole National Historic Site (Sights): A National Historic Landmark that includes the home and studio of painter Thomas Cole, who founded the Hudson River School of American painting.

KINGSTON

  • Four Corners (Sights): The only spot in the US where each corner is occupied by a pre-Revolutionary War building. History buffs will love it! 
  • Lovefield Vintage (Shopping): Located on one of the main drags of the Stockade District, Lovefield Vintage boasts a chic, thoughtfully curated selection of clothing and accessories. It’s definitely more upscale than your typical consignment/thrift store, but you won’t have to rifle through the racks for hours – the owners have edited the selection for quality and quantity. The prices aren’t wildly exorbitant either, given the quality. I picked up a lovely $20 pair of sunglasses that have since become my favorite!
  • Rondout Lighthouse (Sights): One of seven remaining lighthouses on the Hudson River. It’s accessible only by boat, which you can take from the Hudson River Maritime Museum.
  • Rough Draft Bar & Books (Activities): A bustling bookstore/cafe by day/bar by night located on the Four Corners. It can get quite busy, but it’s a great place to hang out with friends, browse the shelves while sipping a warm cup of cider, or get some work done (if you don’t mind the noise on the weekends). It also hosts fun events like trivia night.
  • Vintage Clothing Out of the Past (Shopping): Eclectic, colorful, and filled to the brim with items from the 1940s through the 1990s, this charming consignment store is in many ways the opposite of the sleek, curated Lovefield Vintage a few streets over. It’s ideal for those who like browsing the racks for a diamond in the rough, and the prices are totally reasonable. The owner is sweet and helpful, which is always a bonus!

PHOENICIA

Mystery Spot Antiques in Phoenicia

  • Empire State Rail Museum (Museums): An exhibition gallery featuring old photos and railroad memorabilia. You can also take a mini train ride after you finish exploring the museum!
  • Mystery Spot Antiques (Shopping): Kinda cool. Kinda creepy. Great for those who are into eclectic vintage items and paintings that give you the heebie-jeebies.
  • Whitewater tubing on Esopus Creek (Activities): Rent a tube from Town Tinker Tube Rental for some summer fun on the river. Great for families with teens/tweens and adventurers.

SAUGERTIES

  • Opus 40 (Sights): An abandoned bluestone quarry turned incredible earthwork sculpture park, museum, and gallery by artist Harvey Fite. Architectural Digest deemed it one of “the most beguiling works of art on the entire continent,” while Rolling Stone considers it “the best outdoor performance venue in the Northeast.” Walk over, around, and through the ramps, pools, and fountains of the 6.5-acre bluestone sculpture, then settle back, relax, and enjoy one of the many events and concerts hosted at Opus 40.
  • Saugerties Lighthouse (Sights): A 19th-century lighthouse that doubles as a bed and breakfast. If you plan to stay overnight, book six months to a year in advance because rooms fill up fast. If you’re going for a day trip, there is a small museum inside the lighthouse and 17 acres of scenic grounds to explore.
  • Window shopping on Partition Street (Shopping): Saugerties’ main drag is brimming with cute storefronts and restaurants. Tap into your inner fashionista at Meraki Boutik, get inspired by the adorable home decor at Treasures in the Rough, and soak up knowledge at the Inquiring Mind Bookstore & Gallery.

WOODSTOCK

  • Karma Triyana Dharmachakra Tibetan Buddhist Monastery (Activities): If you’re seeking peace, quiet, and spirituality, this is the place for you. The monastery is a 15-minute drive from Woodstock and guests are welcome to explore its grounds and join one of their classes, prayers, or meditations. The full calendar of events and offerings is available on the Karma Triyana Dharmachakra website.
  • Levon Helms Studio (Activities): A large barn turned music venue/landmark, this was the home and recording studio of the late legendary musician Levon Helms. It hosts intimate concerts throughout the year and will leave any music aficionado in awe.
  • Mower’s Saturday/Sunday Market (Activities): Named one of Fodor’s top ten flea markets in the USA. You’ll find everything from old-school records and vintage clothing to fresh produce. Since it’s so popular, you may want to get here early because parking can be challenging. The market opens at 9 am.
  • Shop on Tinker Street (Shopping): Pick up a beautiful vintage bohemian item at Three Turtles Dove boutique, check out Cedric Martin’s furniture design and woodwork at Pacama Handmade, and indulge your sweet tooth at Fruition Chocolate.

STORM KING ART CENTER: A 500-acre sculpture park located in Hudson Valley’s New Windsor town that boasts over 100 works of art. It is particularly gorgeous during autumn, when the leaves put on a brilliant show of orange, yellow, and red.

However, fall is its peak season, so plan accordingly. Storm King encourages visitors to avoid the busiest days by visiting Wednesday, Thursday, and Friday; if you are going on a weekend, arrive before 10 am or after 3 pm. Public transportation and ridesharing services are also strongly encouraged, given limited parking capacity.

WHERE TO EAT


CATSKILL

  • Gracie’s Luncheonette: Gracie’s is all about locally sourced American comfort foods that they make from scratch – even the condiments are made in-house! You don’t get any more authentic than that.
  • New York Restaurant: Elegant and lively, with live music on the weekends. The menu is a mix of American staples and traditional Polish recipes such as pierogis and golabki.

KINGSTON

Inside the Outdated Cafe

  • Christina’s: Generous portions, good food and service, and a cozy atmosphere. What more could you ask for?
  • Duo Bistro: A good brunch spot that serves classic American food with a twist, like the Korean bistro burger with kimchi and spicy fries. It’s located near a bunch of shops in the Stockade District, making it easy to window shop and burn off the calories from your meal afterward.
  • Le Canard Enchaine: A cozy, intimate restaurant with friendly staff and authentic French cuisine. Try the duck confit, French onion soup, and creme brulee. This is an excellent choice for special occasions, but I recommend making reservations, as it fills up quickly.
  • Outdated: an Antique Cafe: A cute, funky cafe decorated with lots of overstock antique items. Service is gruffer than I expected, but the drinks and pastries are good and it’s a good place to catch up with friends. They also have an Earl Grey latte, which automatically earns them an extra star in my book! I also recommend their apple scone – their scones are their most popular item and they make all of their pastries in house.

PHOENICIA

Lunch at Phoenicia Diner. Look at the size of those salads!

  • Phoenicia Diner: Possibly the most famous diner in upstate New York. As a result, the place is usually mobbed, but the food is quite good and the portions are massive. I particularly enjoyed the fries, citrus glazed salmon salad, and chocolate milkshake. If you’re not super hungry, you might want to split an entree with a friend because – I cannot emphasize this enough – the portions are huge.
  • Sweet Sue’s: Pancakes, pancakes, pancakes. Pancakes are the bread and butter of Sweet Sue’s reputation – literally – and if you’re in the mood for some carby goodness, this is a must-visit. However, I’ve heard their other food items are just ok, so if you’re not feeling pancakes I would visit Phoenicia Diner or one of the many cafes and restaurants in Woodstock instead.

SAUGERTIES

  • Love Bites Cafe: Love Bites has transitioned from a bubbly brunch spot to a healthier, more sophisticated eatery over the past few years, and now it offers more vegan and gluten-free options than the town’s other eateries combined. However, carnivores need not fear: there are still non-vegan items such as burgers and the Filipino beef tapa on the menu. Meanwhile, vegans and vegetarians can enjoy the tofu scramble, cauliflower wings, and vegan pancakes.
  • Miss Lucy’s Kitchen: A rustic farm-to-table restaurant with a daily market menu featuring local meats and produce. Try the Reuben, pulled pork sandwich, and butternut squash soup. It’s comfort food at its best.
  • The Red Onion: If you’re in the mood for upscale dining in Saugerties, this is the spot. Crowd-pleasers include the cast-iron skillet mussels, spicy Thai beef salad, and affogato for dessert.

WOODSTOCK

  • Bread Alone: A family-owned bakery with amazing bread. Their most popular item is their whole wheat sourdough, but honestly, you can’t go wrong. Bread Alone is a carb lover’s dream.
  • Cucina: This rustic-chic restaurant is situated in a restored farmhouse and serves excellent contemporary Italian food. There are communal tables that are perfect for large groups, as well as a dining room for more intimate meals. During summer, you can eat and soak up the warmth on the restaurant’s wraparound porch.
  • Garden Cafe: A trendy, aesthetic vegan cafe and restaurant. There are teas, juices, and smoothies galore, including a “hot shot” of ginger, lemon, turmeric, cayenne and black pepper that can be dropped into a larger juice drink (think healthy Jager bomb). 

 

That’s a wrap! I hope you found this guide to the Catskills and Hudson Valley useful. Three days in upstate New York really is the perfect weekend getaway from the craziness that is NYC (or any big city), and you deserve some R&R. 

So pack your suitcase, stock up on goodies for the road, and get ready for a weekend of pure bliss.

What are you most excited to see/do upstate? Let me know in the comments below!

P.S. If you’re looking for a more international adventure, check out my other travel guides to Istanbul, Uzbekistan, and more!

 

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