The Woodstock Inn – A Luxurious Vermont Getaway

I’ve found that there are a few things that make for a truly great winter weekend getaway. Let’s start with a cute town full of charm and character, add in some amazing outdoor adventures and throw in a luxurious lodge at the heart of it all. This is the Woodstock Inn.

I was graciously hosted by the Woodstock Inn but as always all opinions remain my own. The Casual Travelist contains affiliate links, when you make a purchase or book a hotel through these links the Casual Travelist receives a small commission that helps support this site at no additional cost to you.

Located about 2 hour drive from Boston the town Woodstock in southern Vermont is a postcard perfect slice of New England. This town of 3,000 has a rich history that dates back to 1761 and today the beauty of the Green Mountains attracts both outdoors adventurers and artists of all stripes. A compact main street of charming stone buildings and clapboard cottages that house galleries, shops and cafes as well as one of Vermont’s iconic covered bridges are enough to make Woodstock a great weekend getaway but this town has one more ace up it’s sleeve – one of the best resorts in New England.

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The Woodstock Inn has been a fixture in Vermont since 1793, starting out as The Richardson Tavern (which continues to serve as one of the Inn’s two restaurants serving up steaks and a to-die-for fondue). In 1830 it was expanded to become the Eagle Hotel, and today you’ll find eagles of all shapes and sizes throughout the property as a nod to it’s historic past. The original Woodstock Inn was built in 1892 becoming Vermont’s first winter sports destination. In 1967 the property was bought and renovated by Laurance Rockefeller (yes, of that Rockefeller family) and most recently a $16 million dollar renovation was completed in 2018.

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Today the overall feel of the Woodstock Inn is that of your most stylish friend’s country home – if that home came with an effusively nice staff, two world class restaurants, a luxurious 10,000 sq. foot spa, and activities to suite every taste and season. After a gracious welcome at check in we made our way up to our Tavern King room, and really I could have just relaxed here all weekend and had an amazing time. The decor is classically updated, timeless and not one bit musty or stuffy. Our room was anchored by a supremely comfortable bed with the thickest, plushest pillows I’ve ever slept on. I’m talking serious fluff here that made it awfully tempting to stay in bed were it not for our in room Nespresso (who else gets as excited as I do when your hotel room comes with a Nespresso?). While the decor may be classic plugs and USB ports are discreetly placed on each nightstand. It’s the small touches like these that separate great hotel rooms from the rest.

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The lobby features a huge wood-burning fireplace surrounded by comfortable seating and throughout the Inn I found comfortable little sitting nooks and a library featuring classic games that encourage you to put down the phone and reconnect. At any given time I found people relaxing in the common spaces; whether you choose to tuck into a good book in the Conservatory, play an afternoon game of Scrabble in the library or relax by the fire with an evening cocktail the Woodstock Inn feels much more like a home than a hotel.

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The Woodstock Inn has become famous for it’s afternoon tea and cookies. At 4 pm sharp the Conservatory is by far the most popular place in the Inn with people lining up for delectable scratch-made cookies and tea. Chocolate chip and peanut butter are two of my favorites but I overheard other guests going crazy over the maple walnut.

Pro Tip- Save a cookie to enjoy by the fire after dinner and inspire looks of envy from those around you.

As welcoming as the Inn itself is I came to Vermont for snow and the Green Mountains did not disappoint. While I’m a skier and could have spent all weekend on the runs at Suicide Six (the Woodstock Inn runs shuttles frequently throughout the day), Steve has never caught the ski bug so we opted for non-ski winter fun at the Woodstock Inn’s Nordic Center. Our first afternoon we decided to give fat tire biking a go. It took a minute to get used to riding on snow but in no time we were zipping through snowy meadows and even a few mountain trails. While it’s a slightly different feel that traditional biking Steve and I had a blast and would do it again in a heartbeat.

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The Nordic Center also offers cross country skiing and snowshoeing and since neither Steve or I had ever snowshoed we opted for that. After picking up our gear we headed to Marsh-Billings-Rockefeller National Historical Park to explore the trails on Mount Tom, where on Saturdays throughout the winter a cabin deep in the woods serves up steaming bowls of soup to any skier, snowshoer or hiker lucky enough to stop in.

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After a day exploring the great outdoors I was in need of a little relaxation and knew I would be in good hands at the Woodstock Inn’s Spa. They have a wide range of treatments from facials to body scrubs all utilizing organic ingredients but I can’t pass up a good massage. An hour long massage followed by the eucalyptus steam room and some zen time in the relaxation room and I was blissfully renewed.

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When you visit the Woodstock Inn know you’re going to eat well. In addition to the aforementioned Richardson’s Tavern the Inn’s main restaurant is the Red Rooster which serves breakfast, lunch and dinner as well a craft cocktails at the bar. I enjoyed the breakfast buffet both mornings starting with made-to-order omelets, and of course I couldn’t pass up fluffy Belgian waffles drizzled with local Vermont maple syrup and whipped cream.

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When it comes to dinner the food at the Red Rooster rivals any Michelin-starred restaurant I’ve been to. What hasn’t been grown on the Inn’s own Kelly Way Garden is sourced from the best local purveyors. Pork wrapped in prosciutto is always a good idea, and when it’s stuffed with cornbread and topped with a tomato mushroom ragout it’s divine. When I ordered the caramelized apple dessert I was expecting a rustic apple tart but what came to the table was a work of art. A sable crust was topped with cinnamon mascarpone, pear Bavarian cream and a whimsical spiral of spun sugar, it tasted even better than it looked.

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The Woodstock Inn boasts a beautiful property with the stunning backdrop of the Green Mountains but what makes it a truly special place is it’s people. I was welcomed like a dear friend from everyone I encountered and it’s this gracious spirit that will bring me back to Vermont’s prettiest address.