Natty Adventures in The Berkshires

Living in New York City is awesome but, in the winter especially, it can be tough.  Slushy sidewalks, jacked up Uber rates and tiny apartments can make even the happiest New Yorkers go stir crazy. But if you don’t have the time or the budget to jet off to the Caribbean, there are plenty of options to unwind much closer to home.  I recently checked out the Berkshires: the bucolic mountain region in western Massachusetts that’s easily reachable by car or train. 


Don’t worry, just because you’re spending a weekend away from the pulse of the city doesn’t mean you need to stay in a Victorian mansion filled with spiderwebs, or join the senior citizens in a doily filled diner.  


Click through for the coolest places to stay, eat and do for the discerning New Yorker (read: you) who’s ready to unwind. 




THE RED LION INN – For over 200 years, the Red Lion Inn has been a staple in the Berkshires.  The charmingly mismatched décor make the rooms feel more like staying in someone’s home than a hotel.  There are multiple spots for dining and entertainment on the property, making it easy to stay and never leave.  The Red Lion also prides itself on its eco friendly practices and makes an effort to support the local community and food purveyors. 


APPLEGATE INN – If it’s romance you’re after, look no further than the Applegate Inn.  A few of the rooms have in-room fireplaces and claw footed tubs, and lofted down bedding will keep you cozy on cold nights.  If you can drag yourself out of your room, shuffle downstairs to the common area for complimentary wine and cheese by the wood-burning fireplace. 


RACE BROOK LODGE – If you loved camp as a kid, The Race Brook Lodge is for you.  This compound of cottages is nestled along a tree-lined river, studded hammocks for the warmer months.  The sprawling property also includes a large barn available for special events, and a coach house with an open kitchen for those looking to cook at “home”.  An eclectic mix of native American blankets and antiques give Racebrook a bohemian, rustic vibe. 





HIKE - When a walk through Central Park just won’t cut it, take a hike up to Monument Mountain.  The rocky mountain trail is about 1.5 miles and will take you about 2 hours, round trip, to summit.  The views from top are worth the effort, but the tall mossy trees and craggy rocks throughout will keep you enjoying every step. 


SPA – Reward yourself after a day of hiking with a luxurious massage or facial at the Cranwell.  Built in the 1800s, the historic structure was once owned by Harriot Beecher Stowe, and is now arguably the regions most elegant hotels.  Whether or not you stay in one of their luxurious suites, their spa and sprawling grounds are worth a visit. 


SHOP – While it’s not exactly a place to stock your wardrobe, there is plenty of shopping to be had in Lee, Great Barrington and Stockbridge.  Take an afternoon to wander the main streets of one or each of these towns (they’re not far apart) perusing the various general stores, candy and gift shops.





HAVEN CAFÉ – Even if breakfast is provided where you stay, Haven Café is worth paying for.  This casual eatery (also open for lunch) will have you drooling upon arrival.  Start with a melt-in-your-mouth dill biscuit and matcha latte, and move on to one of their epic egg scrambles or croissant French toast – also available in a gluten free version for those looking to indulge (semi) responsibly. 


CHEZ NOUS – With a menu that changes daily, you may not know exactly what to expect at Chez Nous, but you know it will be good.  This French bistro is the love child of a French chef from Brittany and a Le Cordon Bleu trained American pastry chef.  The result is food worthy of refined city-spoiled palates, with a relaxed homey vibe.   Grab a seat on the porch if the weather is warm, or snuggle up at the bar with a glass of Grand Marnier. 


STAGECOACH TAVERN – Imagine the coziest bar / restaurant you’d hope to find in a country town, and you’ve got the Stagecoach Tavern.  The multilevel space is topped with wood beamed ceilings and offers umpteen nooks and crannies for dining parties big or small.  But the money spot is at one of the small tables near the bar side, directly in front of the roaring, wood-burning fire.  Chances are, even if you come in for just a drink, you’ll wind up staying for the herb roasted chicken or bacon mac and cheese… You wouldn’t be mistaken. 

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