As much as I try to embrace the cooler weather each year, it always bums me out a little after a couple of weeks, and I find myself looking for ways to make the best of it. Well this year, my sister Julia came to the rescue when she recommended we take a spontaneous trip to Woodstock, VT. We would have gone anywhere, really – there’s no shortage of autumn-y things to do when you live in New England – but we had discovered Woodstock through some favorite Pinterest boards recently and decided to check it out. As frequent visitors to Vermont and New Hampshire as kids, it’s kind of hard to believe that neither of us had ever been!

So on a chilly, cloudy Sunday morning, we piled into Julia’s bright red Volvo, stocked up on scones and iced chai’s from 3 Little Figs, and were on our way. The two-and-a-half hour drive didn’t scare us! Sisters never run out of things to talk about, after all. By the time we passed through New Hampshire, the sun was shining and we were daydreaming about all of the things that awaited us in Woodstock.

 

And boy, did Woodstock live up to our expectations – and more! Talk about a quintessential New England town – complete with a quaint main street, commons, town hall, library, cozy restaurants and enticing store fronts. We were in heaven.

Our tummies were rumbling by the time we parked (and we did a little dance when we realized that street parking is free on Sundays when you live anywhere but a city!), so we popped into the first restaurant we found – Bentley’s. Oh, Bentley’s. As a lover of all things cozy, I was right at home. Julia planted herself across from me on a gorgeous but oh-so-comfortable antique sofa, and we stared in child-like wonder at the whimsical Christmas decor, including ornaments strung from the ceiling. The menu was everything we could have wanted – warm soups and creative salads and toasty sandwiches – it was so hard to choose! The most important decision was what to drink, anyway.

 

A couple of warm cider drinks, a yummy salad, and a locally-sourced club sandwich later, our tummies were satisfied and we were ready for some explorin’.

 

We popped right into F.H. Gillingham & Sons General Store across the street and were immediately overwhelmed with the feeling that we needed one of every single thing. Despite the shelves of blankets and mugs and socks and mittens and books and paper goods and candles calling our names, we escaped with just a few small treasures. Every store we entered was cozy, warm and oh-so-charming, and the people couldn’t have been friendlier. A favorite was Ellaway’s Attic Consignment shop which boasted so many beautiful and unique antique pieces – all at a steal of a price!

 

Our explorations (and once again, our tummies) took us down the road to the Woodstock Inn and Resort. After standing out front for who-knows-how-long, mouths hanging open at the wonder of it all, we snuck inside to look around. The universe was on our side that day and we arrived just as tea and coffee and fresh-baked cookies were being put out in the conservatory. We cozied up in comfy chairs, sipped on hot chocolate, and munched on cookies while our noses defrosted from being outside. I truly cannot think of a cozier place.

 

After some more exploring of the gorgeous inn (the game room and courtyard were both favorites!), we ventured across the street to admire the covered bridge. Of course there was a covered bridge. It is Vermont, after all.

 

By that time, the sun was setting and the shops were closing, so we hopped in the car and headed for the Woodstock Farmer’s Market for some maple syrup and apple cider to go. And of course a cheese sample or two. Or three…

It still felt early but was getting quite dark, so we took the back roads out of town and started to head home. Just when we thought our day was over, we turned a corner to be met with the glowing windows of Simon Pearce. We of course couldn’t stand the thought of our adventures being over, so we decided to pop in for a look around. Julia recognized the brand from her job at a boutique that sells the gorgeous glassware, and I recognized it from my unhealthy obsession with Martha Stewart who had featured Simon Pearce on her website. We marveled at all of the gorgeous glassware, and were delighted to find the glassblowers downstairs creating each piece by hand! We could have watched them make water goblets all day. If you visit, be sure to walk around the glassblowers to the back door where you’ll get up close and personal with the waterfall you likely passed on your way into Woodstock!

 

And just because we hadn’t already had enough to eat that day, we sat down at the restaurant upstairs for some wine and a cheeseboard. Because if there’s a cheeseboard, it’s pretty much required eating. The staff was so friendly and kind and kept us entertained while we sat.

We honestly could have sat there for days, but we begrudgingly remembered the long ride home that awaited us and piled back into the car, waving goodbye to Woodstock and knowing that we will be back very, very soon.

 

Have you been to Woodstock? What did we miss? What are you favorite small towns to visit when it’s chilly in New England? Let me know in the comments!

xo,

Kelly