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10 Hidden Gems in Upstate New York and Connecticut

Upstate New York on its own doesn’t get nearly enough recognition. After all, when the “Big Apple” is right around the corner, the tourists will naturally be drawn there. However, if you are from New York City and trying to get away for the weekend, or you’ve simply never been attracted to the major tourist towns, you might be wondering what else New York State has to offer. Rest assured, there is plenty, and luckily for you, most of them are still relatively undiscovered. Here, we have collected some of our favorite secret destinations across the state, so you can easily pick your favorite and start driving. If you’re feeling really ambitious, you could even plan an entire road trip around upstate New York, taking in all the finest things it has to offer.

Gather Greene

Gather Greene is a “boutique hotel” comprised of mini cabins in the woods in Greene County. They are designed with a minimalist approach to luxury, and each features large glass windows and walls for a fully immersive forest experience. They are nestled into a 100-acre property skirted by mountains, and they even have an old quarry onsite for romantic afternoon swims. Gather Greene has both indoor lounges and outdoor pavilions for when you need a break from the elements and they also have a “boulder bar” for sipping cocktails under the stars. If you like sunsets, meadows and bonfires, you will not regret booking a trip to Gather Greene.

Urban Cowboy Catskills

Urban Cowboy Catskills is truly a unique experience you will not find anywhere else. This expertly designed modern and extravagant twist on a ranch lodge will blow your mind. Their guest suites are lavish yet rustic, and feature gorgeous copper clawfoot tubs you will be super excited to take a soak in. Only 2.5 hours outside of New York, this 68-acre retreat is the perfect place to escape into the mountains while still feeling like you are on a luxury hidden getaway.

Terrain Garden Café

Terrain, located in Westport, CT, is a sweet farm-to-table restaurant you need to visit. For most of the year, you can enjoy a meal in their indoor dining area, which has ample windows for an indoor/outdoor feel or their regular outdoor patio. This magical setting is very unique, since you’ll be dining among extravagant and vibrant plant life. They have an amazing menu with healthy vegetarian options as well as local staples. We recommend visiting for brunch, enjoying a fresh smoothie and then exploring the greenhouse to transport yourself to another world.

The Amsterdam

Among some of the other finest farm-to-table restaurants on this list, The Amsterdam in Rhinebeck is not one you will want to miss. Foodies will adore their approachable menu of complex and locally sourced dishes. Guests can choose between a highly modern, minimalist indoor dining room and bar area, or a laid-back, picnic-style outdoor patio, where you can even opt to enjoy your extravagant meal in wooden lounging chairs around personal fire pits. On a trendier note, you will certainly want to snap a picture of your cocktails, which just might be served inside an ice block.

Walkway Over The Hudson

Assuming you are not afraid of heights, hiking the Walkway Over The Hudson State Historic Park loop trail is an experience that should be on every New Yorker’s bucket list. Accessible year-round, the trail includes two long bridges which cross above the Hudson River at 200+ feet. The views from up top are unparalleled and are equally as dramatic in Winter or in Summer. It may even be worth a visit in each season since the backdrop is so drastically different. The path itself is not overly long or challenging, making it perfectly suitable for beginners on an afternoon nature walk.

Hiking and Swimming at Fawn’s Leap

Near Kaaterskill Falls in the Catskills Mountains, there is a 40-foot cliff with gently cascading waterfalls and a perfect grotto for an afternoon swim. This spot is the Catskills’ best kept secret, and is rarely occupied, making it a great place to escape and enjoy nature. If you are an adrenaline junkie, you may also like to know that those who visit Fawn’s Leap frequently state that it is the perfect place for swimming. Just a pro tip - be sure to bring goggles so you can discover the rock formations under the surface.

Area Two Experimental Brewing

If you live for a good microbrew, you will love visiting the unique brewery in Stratford, CT. Essentially, Area Two is a secondary, 10-acre brewery where experimentation is the name of the game at Two Roads Brewing. There is a constant rotation of new and exciting beers to try, and you can expect to find flavors and perhaps even types of beer you have never tried before. If you’re not usually the type of person to order a flight when you visit a brewery, now just might be the time to try one out so you don’t miss any of these cool new creations. Complement it with some artisanal cheeses.

Dine at Blooming Hill Farms

Dining at Blooming Hill Farms is a real treat. Not only to do they grow much of their own organic and locally sourced ingredients, but you also dine in a greenhouse-like atmosphere which will give you majorly relaxing, earthy vibes. If you love wood fired pizza and amazing craft cocktails, you’ll want to be sure to visit for dinner. However, if you love brunching with friends, consider switching brunch to Blooming Hill this weekend and you will not be disappointed. While visiting the farm, you will also be able to walk around the property and visit the farm shop to pick up produce and other artisanal goodies.

The Glass House

The Glass House, located in New Canaan, CT, is developed out of the private residence of artist Philip Johnson, best known for his architectural work over the past century. The property is large and features many trails of dwellings that are renowned for their architectural design. You can book one of several tours of the Glass House property or wander on your own with as much or as little walking as you see fit. While some tours require very little physical activity, you can also participate in a walk that is just over a mile long. The more walking you are willing to do however, the more of the property you will be able to experience including studios, galleries and outdoor sculpture exhibits.

Grace Farms

Grace Farms is an 80-acre property globally known for its impressive architectural designs and dwellings. The river building attempts to connect multiple community spaces under one roof and is home to multiple collaborative spaces including amphitheaters, libraries and tea rooms. The building itself is marvelous to explore, weaving in and out of its indoor/outdoor spaces, but you will also enjoy exploring the trails throughout the property. 77 of Grace Farms’ acres have been protected, and you are welcome to walk through trails around the forests, wetlands, marshes, ponds and meadows.

Well, there you have it. If you have been looking for a secret destination for your next getaway, you have certainly found one. We hope you enjoy discovering all of these hidden gems, and hopefully finding a few more of your own along the way.