Woodstock, Vermont Wassail Weekend

My “Christmas spirit” was severely lacking earlier this month.  Are you familiar with that old Faith Hill song “Where are you Christmas”, from How the Grinch Stole Christmas?  I felt as if I was walking around with that playing on a constant loop.

This was weird for me.

I am actually someone who typically (annoyingly) belts out that song, and any other holiday tune that comes to mind to anyone who will listen to me.  I start slowly pulling out my decorations in October; of which there are many.  I keep running lists of the gifts I want to buy for people, all year long.

But this year, meh.

I am not sure what brought this about…maybe I was too focused on a couple of the long-term projects I’ve been working on.  I tend to hone in like a laser (Eye on the prize, you know?) and am practically bursting at the seams to complete and share some things with you in 2017.  Or perhaps, I was just too far in my own head.  There is a part of me that felt very “How is it December, again“?  This year flew.

What I do know for sure is that when I get into that space, the best thing I can do is to “go”.  It can be anywhere really.  There are plenty of country roads near my home that I can ramble down, trails to hike, or sweet small towns to visit.  I’ve never shied away from booking a plane ticket either.  I like to get lost, and simply put, it’s the best way for me to get back to myself.

In this case, I found the happy medium with a road trip to Woodstock, VT for Wassail Weekend.  It was either an instance of extreme serendipity or of astute Facebook algorithms, but I was seeing mentions of this festival everywhere!  All of the photos I clicked on looked like scenes straight from a Currier & Ives print, so I figured if there were any place I could find a bit of that Christmas magic, it would be there.

I was right.


I took approximately 987,654 photos for you, but in words, these are a few of the things that I loved about this beautiful celebration (and place):

The decorations!  Not a corner of Woodstock was left untouched.  Even the cars were decorated!  Each home, shop, and restaurant in the very least had a wreath, and all were so unique and fitting to their locations.  I loved that the Vermont Flannel Company for example, had potted trees outside their storefront with flannel bows tied to them.  My favorite display, however, was the big sleigh, which was perched in front of a flower shop.  The door to the shop was covered in lit garlands and twigs and dried flowers; so gorgeous.

I realize that I had a pretty limited scope, but I felt a true sense of community in this town.  The people that I met seemed genuinely excited about the goings on, and were eager to share not only information about Woodstock, but to lend a helping hand in general.  All of the businesses were extremely crowded by the end of Saturday, visitors were lost, and it was freezing cold outside to boot – but there was nary (from what I could see) a Scrooge in sight!

This is somewhat in keeping with the above, but I went into several restaurants while I was there, and each one had a chalkboard or visible menu that listed all of the local products and ingredients that the establishment was using, all the way down to the Farmhouse Pottery I was eating out of.  We have a little bit of this in Upstate NY, but it would make my heart happy to see more of it.  Coming from a family of small business owners, I know that this is how small businesses grow; through sharing and support, starting in their own communities.  It’s such an awesome thing.



If you decide to visit Wassail Weekend next year, or somehow stumble upon this post in the meantime, here are a few of my tips:

I highly recommend taking the Holiday House Tour.  I also recommend wearing a pair of slip-on shoes.  You’ll have to remove them and put on paper booties at every stop, and with most of the entryways being packed, it’ll be much simpler to pull your shoes on and off.  I would bring an extra pair of warm socks as well – especially if there is snow on the ground.  In spite of everyone’s best efforts to keep them dry, the changing areas were a bit wet and in turn, my socks were too by the end of the tour.

If you like to take photos as much as I do, definitely wake up early!  I was out the door by 7:30 am, and it made all the difference in being able to get pretty shots of the covered bridge, the wassail setup, etc.  By noon, the town was an absolute zoo!

Book your accommodations early too!  The Inns in the neighborhood fill up fast and there are only so many rooms to go around.  If you can’t stay directly in town, I would advise you to drive in early, to find parking.  Planning on leaving after the Horse & Carriage Parade?  Park on a side street facing away from the Village Green.  This is the main thoroughfare for the parade so it will get very congested immediately thereafter.

In addition, I would reserve time to drop by the businesses outside of the main drag.  My favorite place in Woodstock was Farmers’ Market; a very well curated assortment of area produce, gourmet food, fresh flowers, and Vermont goodies.  I bought all of the maple things, picked up a few gifts for my family, and left with an armload of festive bouquets of Boxwood and Protea.

In my opinion, one of the best parts of a road trip is the random pull-overs you make along the way.  Of course this will depend on where you are headed, but I would suggest giving yourself ample time to get to and from Woodstock so that you can do that.  I stopped in a couple of towns en route, and for the record could have spent the entire weekend in Northshire Bookstore, in Manchester.


It had been a bit since I’ve driven through Vermont, so I’d almost forgotten how pretty the roadside scenery is.  As I was heading home – feeling warm and fuzzy as it was – the sun was setting all shades of pink and gold and fire, and I passed one of those iconic red barns with a decorated sleigh hitched and ready to go perched to the side of it.  It’s hard to describe exactly what that looked like; the horses stomping in the snow, with a group of merry people bundled up, ready for their ride.  To say it was one of the most beautiful images I’ve ever seen would be an understatement.

Spirit restored.

I hope that wherever you are, you’re still enjoying all of the celebratory feels, and looking forward to a bright and shiny new year.  A belated Happy Holidays, and an early Happy 2017 to you!  XX


8 Responses to Woodstock, Vermont Wassail Weekend

  1. katelon says:

    Great photos and posts. Happy New Year!

  2. There is no shortage of lovely towns, across New England and northern New York. Bennington has been my favourite, but Woodstock certainly looks inviting. Happy 2017, Carlynn!

    • jjbegonia says:

      Yes, you are right; they are many lovely places to see and visit! Bennington is wonderful – I really like the “Bringing You Vermont” store there. : ) I hope that 2017 is treating you well so far!

  3. Anonymous says:

    I garnered a slew of memories from spending time in Woodstock. Your amazingly beautiful photography sent me back in time and made me want to experience the holiday season all over again! Thanks for taking me there!!!

  4. pamela devling says:

    I have been looking into going here this coming Holiday. I’ve read lots of reviews, blogs and articles about Wassail Weekend. But yours is by far the best. I’m so happy I happen to stumble upon your blog. You have painted an image in my mind of everything you would expect in a Hallmark movie. Your photos are an added bonus. May I ask where you stayed when you were there? I’ve narrowed it down to 2 places and am hoping maybe you can help make my final decision. Thanks!

  5. Pamela Devling says:

    I am planning on attending the Wassail Weekend this coming year. I have read lots of reviews, blogs and articles, but your blog was by far the best yet. I just happen to stumble upon you and I’m so glad I did. You have painted an image in my mind of a place right out of a Hallmark movie and your photos were an added bonus. Could you please tell my where you stayed? I’ve narrowed my search down to 2 places and maybe you could help me make my final decision. Thanks!

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