Off Season Couples Catskills Getaway

Adventure, Peace, Beauty and Good Eats!

Why a Catskills Getaway?

The Catskills have always been a beloved ‘back to nature’ getaway. From historical artists to the Borscht Belt resorts of yesteryear (you know what I’m talking about Marvelous Maisel Fans) to Woodstock there’s always been magic here. Now Millennial artists, bakers, hoteliers, and restaurateurs are shaping the next ‘version” of the Catskills celebrating the same awe-inspiring surroundings. It’s only 90 minutes from NYC and about 3 hours from Boston but you might as well be a world away from the crowds, noise and hurried life.  Trust me, it’s one of the best winter getaways in New York or off season weekend escape!

Celebrating our Wedding Anniversary 


Fifteen years ago we bought a Catskills timeshare in Hunter, NY – –  a mostly undeveloped mountain and forest area rich with hiking, skiing and history close to several major cities in the Northeast. We loved how easy it was to get to, enjoyed the drastic change of pace, and were young (READ:  kinda crazy) so we decided to buy a fractional ownership timeshare at Kaatskill Mountain Club. Since 2005 we have been enjoying “getting away from it all ” year round with our friends, babymoon-ing and celebrating anniversaries!  It’s also fantastic for family trips – if you’re interested check out my separate post here. 

So, 95% of the time we stay at our timeshare. We like having a kitchen even just to make our coffee how we like it.  We love the extra room a condo provides so one person can be a sleepy head as long as they want (Guilty, as charged)! We love to chill in the year round pool and relax in the hot tubs with a drink and just be able to have adult conversation with each other!

Besides our timeshare, we have stayed at the larger townhouses on the other side of the ski slopes a handful of times. One time we needed more space for family, and the timeshare was sold out due to a wedding, so we rented a townhouse on AirBnb. If you are coming for a Beer, Wine or Music Festival on Hunter Mountain grounds staying “on-property” really does make it a lot more convenient….. you can just stumble back to your place!

If you’re looking for other Catskills lodging options than Hunter Mountain properties there are lots of choices! For a hotel experience, I recommend the recently renovated Scribner’s Lodge, a beautiful modern designed luxury hotel with new owners. They have larger suite rooms, a pool that’s open in the summer, an amazing bar, and a restaurant that is definitely more Manhattan-ish.   Or, AirBnb and VRBO have lots of amazing rental options in the Catskills ranging from the traditional A-frames, cabins, large homes and even tiny houses.




Last Chance Cheese (Tannersville, NY)

I have a SERIOUS love affair with this homecookin, relaxed cafe! For 15 years, we have eaten here on every single visit – it’s my happy place!  It’s not a Catskills vacation until I have the Meat and Cheese Board with my favorite beer, Franziskaner Hefe. They have a wonderful extensive Americano menu with Gluten Free sections, 300 specialty beers, 50 whiskeys and 100 cheeses!  We have come here straight from a hike at Kaaterskill Falls all muddy and gross and have also enjoyed it for dinner.  They have a new live music venue on the other side of the store, so dinner+ concert combo is a great night out all in one place. 

Jessie’s Harvest House (Tannersville, NY)

If you are looking for a more elevated meal and/or are fans of the infamous Blue Stone at Stone Barns, this is the dinner spot for you!  Recently opened by a former Blue Stone chef and granddaughter of the founders of Hunter Mountain it is one of those places where the food is fantastic, but the atmosphere is casual.  They have great mixed drinks, Pat LaFrieda burgers, Meatballs and pasta! Definitely make a reservation if you’re planning on enjoying this restaurant – – even for the Early Bird Special time slots!

The Catskill Mountain Country Store (Tannersville, NY)

If you’re looking to go out to breakfast, brunch or grab a treat this is the place! They serve breakfast all day.  If you slept in (no kids early wake-ups, woohoo!) you don’t have to worry about rushing out to grab breakfast. If you never make it here during your trip, you have to stop on your way out of town and get Apple Cider donuts for the ride home.  When Hubby goes to Hunter for guys trips he knows he must come home with some for me, or there will be a very sad wife. 

Twin Peaks Coffee and Donuts (Tannersville, NY)

Speaking of donuts, let’s talk about the made to order donuts and homemade coffees at this place! Just north of downtown Tannersville is this wonderful (and popular!) cafe. If you drive by on the weekend you’ll probably see the line out the door, it’s that good!  You can’t go wrong with any donut pick and make sure to ask what coffee flavor mixes they made from scratch — we can’t get enough of the Pumpkin Spice one. 

Rip Van Winkle Brewery Company and Restaurant  (Catskill, NY)

If you’re looking for a place on the way to/from this restaurant is a great pick!   We first discovered this place on a couple trips when we stopped in to try the locally brewed beer (they have 7 in total). We spied a large brick pizza oven and returned for some pizza another time. I’m not surprised that the owners are from Sicily with the delicious pizza and Italian dishes they serve. Hubby and the guys love the burgers here too!



North/South Lake ( Hunter, NY)

This state park dubbed “America’s First Wilderness” has so much to offer you could spend a whole week here! Located 15 minutes from Hunter Mountain, this 1,000 acre preserve with two lakes has not only history, fishing, canoeing, paddle boarding but hiking to some of the best views and spots this region has to offer— all for $8 a car!

 If you are a fan of history, paintings, the Hudson River School of Art, or want to be a little more *extra* check out the “Step Into A Landscape Painting” site that shows you how to go to the exact spots of infamous paintings almost 200 years ago. Three of their highlighted locations are in North/South Lake. 

© Thomas Cole National Historic Site

Don’t forget to pack lunch, snacks and drinks for the day, as there is no food service in the park. Twilight General Store is a popular stop right on the way to North/South Lake, and is that last store before the park entrance. 

Kaaterskill Falls  (Hunter, NY) 

You can’t come to the Catskills and not see the highest waterfall in NY State and the inspiration for centuries of folklore. There are lots of different viewing and hiking options which I’ve outlined in a separate post here. There’s options for every ability level, and if you only have 20 minutes, you can still do it! It’s a must do. 


Hunter Mountain Activities

Scenic Skyride

Running Spring, Summer and Fall the ski lift takes you to the Summit of Hunter Mountain –  3,200 feet up. On a clear day you can see the peaks in Massachusetts and Vermont. If you visit in the fall, the foliage views are breathtaking.   If this is on your must do list, try to go in the morning or you’ll probably wait in a long line with wedding guests heading to a wedding ceremony at the Summit. 

New York Zipline Adventures 

Ten years ago, this company opened up at Hunter Mountain and now offers four adventures. The Mid Mountain Tour (Day and Night) is great for those who have never been ziplining before. The SkyRider features the largest, longest and fastest zipline canopy tour in North America – it is no joke! Either way it’s a thrilling option for you adventure seekers and a great way to see beautiful mountain scenery. 

Night Life

Last Cheese’s Music Tavern (Tannersville, NY)

In 2010, the restaurant owner’s son opened up a music and late night venue in the adjacent building of Last Chance Cafe. Friday and Saturday nights, year round, the Tavern features great regional acts from rock, folk and country playing crowd pleasing sets. Enter the tavern through the secret entrance in the restaurant’s gourmet shop that magically appears at 7pm. Admission is free, so come for a couple of songs after dinner or stay all night.  Enjoy one of 300 specialty beers, 50 whiskeys and my personal favorite — a cheese plate from their 100 offered cheeses. 

Scribner’s Catskill Lodge (Hunter, NY)

Hunter’s latest luxury renovation, this hotel has an equaling impressive circular bar and mountain views. Whether you enjoy a cocktail in their indoor cozy space or outdoor deck, they are soooo good! Their Queen Bee whiskey cocktail is very popular. They released this recipe during COV-19 to make at home. It’s always happy hour somewhere 😉


Jägerberg Beer Hall and Alpine Tavern (Hunter, NY)

A modern take on German classics ( plus seasonal fare) by a CIA grad with a large selection beers, wine and cocktails. I’ll take a Hefe with a soft pretzel and schnitzel here any day!   “Jagerberg” (German for Hunter Mountain) reflects its close mountain proximity in a newly renovated space and makes a great combo after mountain based activities. 

Hunter Mountain Brewery ( Hunter, NY)

This casual brewery features beers, lots of cocktails and pub food. The large bar area and oversized deck are popular hangouts year round.

Rip Van Winkle Restaurant ( Hunter, NY)

Located at the Kaatskill Mountain Club Condo hotel, the lively bar scene draws regular locals as well as guests of Hunter Mountain properties. Surprisingly for a hotel bar, they have killer happy hour specials and great food (lead by a French chef ).

Hunter Mountain Festivals:

Oktoberfest  (October)

Hunter Mountain’s award-winning  four weekends of Oktoberfest is not only a blast but admission is free!  Each weekend has different specialties – – Cider Brews, a Wine Tasting, rally car racing and off roading adventures. They have traditional German bands and dance groups providing entertainment all weekend. Grab a beer in a boot, enjoy the show and perhaps join the dance floor. Or outside there is a variety of food, activities and rock bands playing.  

 We have attended Oktoberfest as both a family and just as a couple. When we came up just the two of us, we timed it to the Wine Tasting weekend and had a blast. Off in a separate area of Oktoberfest, for $20 you can taste local wines all day long (in and out privileges). We enjoyed talking to some of the producers, learning more about their stories and wine. We bought bottles of some of our favorites and enjoyed them back in the hot tub. It doesn’t get much better!

TAP NY  (late April)

TAP NY Beer and Food Festival has grown since its start 20 years ago at the Hudson Valley campus of The Culinary Institute of America and is now NY’s largest craft brew, wine and food festival. They have 120 beers from all over the state – – which is producing some pretty amazing beer! Brewery Ommegang is one of our personal favorites. The event features great food pairings, with some small food samples along the way, as well as live music. Designated a Top 10 Beer Festival in America, event tickets start at $70, and is really a good time!

TrailBlazers Country Music Festival (June)

Formerly the Taste of Country Music Festival, this 3 day festival in June  brings A-List country music stars to the Catskills. This Virginia girl loves country music, so this is big! The previous headliners have been Dierks Bentley, Luke Bryan, Keith Urban, Rascal Flatts, Little Big Town, Brooks & Dunn, Florida Georgia Line and Sam Hunt. I would love to see more than one woman headliner, but that’s a conversation (or rant!) for another time.  If you’re a country fan, like their event Facebook page as tickets sell out quickly. Summer nights, ya’ll!

Come and see what all the love is about! Let everyone else wait in endless traffic to go to the Hamptons – – You’ll be in the ethereal Catskills before they are even on the Long Island Expressway!


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