A Quaint and Charming New England Weekend in Woodstock, Vermont

It’s hard to imagine a place more picture-book New England than the charming shire town of Woodstock, Vermont. My family and I just had the privilege of spending four beautiful July days here for the most memorable family wedding.  Whether you are the skiing-hiking-kayaking outdoorsy type, an avid antiquer, foodie, or  wine/ beer connoisseur, Woodstock will fulfill all of your New England desires.

I have personally not been to Vermont since I was a child. We used to spend winter weekends skiing at Killington Mountain, a quick and scenic 25 minute drive from Woodstock.


While Woodstock is currently bursting with charming country gardens planted along white picket fences, I could not help but fantasize about the arboreal kaleidoscope that exists during the Autumnal months, or the cozy cup of cocoa in hand while strolling down sparkling snow-covered streets,  trees adorned with twinkle lights during winter. No matter the time of year, a trip to Woodstock, Vermont will fill your heart and soul with pure New England charm.  National Geographic actually described Woodstock as one of the most beautiful small towns in America.




We spent three fun-filled nights at the River House Suite at the Shire Woodstock Inn–the gem being a massive deck overlooking the meandering Ottauquechee River. Hollyhocks, zinnias and all kinds of country garden flowers surrounded the Shire Inn, giving it a true cottage feel on the exterior, while we thoroughly appreciated the luxurious upgrades of the interior.  The abundance of space was perfect for a family of six, with dozens of guests stopping by for pre-dinner cocktails in the living room and outside on the expansive deck.  The convenience store directly across the street couldn’t have made entertaining easier. Another wonderful aspect of The Shire Inn is that they have been named a Green Hotel by the Vermont Department of Environmental Conservation. They are committed to being environmentally friendly and sustainable. Even their brand of shampoo and lotion are a bee brand that has a mission in saving bees. They are also a pet friendly hotel.

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A stroll around the town began by walking right out of our front door. In each direction you look, you will  feel like you’ve traveled into the past, yet this historic quaintness was paired with a contemporary feel–the perfect balance for an east coast weekend getaway. The leisurely morning walk to the Soulfully Good Cafe for a delicious outdoor breakfast was a lovely start to the day.  (Also a pet friendly establishment)

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After breakfast, it was so much fun browsing the shops and galleries, and walking across the covered bridge that spans the Ottauquechee River.  An invigorating hike with the bridal party filled our lungs with fresh morning Vermont air.


In the center of town is the village green surrounded by beautiful architecture, from Federal mansions to a Greek-Revival courthouse and a Romanesque-style library. Quaint restaurants, ice cream shops and breweries also line the charming streets.



The wedding was held at the beautiful Woodstock Inn.  We are all still in awe over every detail of this breathtaking venue and memorable family event.




The majestic mountains and gurgling rivers balanced with New England elegance and history, make Woodstock, Vermont the ideal escape for an East Coast summer retreat, festive fall excursion or a crackling fireside winter ski weekend getaway.






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