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10 Things To Do If You're Spending The Holiday in Woodstock

Oct 27, 2020 03:49PM ● By Kaitlyn Malone
Over the holidays, we hope to experience certain comforts and treat ourselves to some serious holiday cheer. This includes eating lots of good meals, taking a walk in a "winter wonderland" or through an idyllic town decorated with lights, and then cozying up with a fuzzy blanket while listening to holiday music and watching our partner bake a pie. Let's face it; food is one of the most important parts of the holidays. A good meal makes us feel nurtured and can bring us into the moment in appreciation as we connect with our loved ones and with strangers. This is why I will be mentioning a few restaurants, among other things that are important to experience while visiting Woodstock this holiday season!

When you spend the holidays in Woodstock, you can indulge in all of these things and more.  Woodstock has amazing restaurants to eat in (or order out), idyllic Inns to stay in and relax, adorable family-owned shops, and breathtaking countryside to walk through.

Here are 10 things to do if you are spending the holidays in Woodstock:


The Woodstock Inn & Resort

There are many places to stay in Woodstock during the holidays that would be amazing, and you really can’t go wrong. That being said, the Woodstock Inn is truly a must-see, and if you can spend the night, weekend, or week there, you will not be disappointed. Travelers come from all over the country to stay in the elegant and cozy rooms and appreciate its classic charm and warmth. After a walk through town, you can relax at the Woodstock Inn’s spa or cozy up at the outdoor fireplace in the snow with some hot cider. This establishment also offers various festivities over the holidays, so be sure to check them out on their website to see what’s available!

The Prince & The Pauper

This restaurant has been serving satisfied guests for around 46 years. It is located at 24 Elm St in Woodstock, VT. It has an elegant and relaxed atmosphere with incredible food and service. They have an option for a three-course Prix Fixe menu, including your choice of Appetizer, Salad, and Entrée, which will be incredibly scrumptious. Be sure to make a reservation in advance! You can always pick up your meal to go if you prefer to have a more intimate meal at your B&B. Check out their website here for more info on their winter menu and for any updates,


This restaurant is a must-see. It is a restored 19th-century mill that overlooks a waterfall! Just imagine taking a bit of your delicious food and taking in the sites of a snowy bank. This restaurant serves refined American food. Be sure to make a reservation here as well as they are following the social distance protocol, and space is limited. This establishment is an easy drive from Woodstock and well worth it. For more information and for any updates, check out their website here.

For a more low key dining option this holiday, check out the Worthy Kitchen. It is a cozy bar and restaurant you can walk to in town that serves American meals and is vegetarian friendly. Like most of the restaurants, they use a lot of locally grown ingredients, and you can taste the freshness. You satisfy your cravings from Mac and Cheese to a hamburger or a spicy tuna poke bowl. Here is the website for more info.


For a taste of something different, try out Angkor Wat, which serves Cambodian fusion cuisine. This restaurant has a lot to offer. Perhaps you can stop off here after a lovely walk in the snow for a hot bowl of soup, one of their traditional Cambodian dishes! Here is their website for a full menu. 


You simply must stop into Gillingham’s General Store when visiting Woodstock, Vermont, this holiday. It is an incredibly charming, family-owned shop. Step in and take in a bit of holiday magic as you peruse the shelves for a treat or two. I think they have some chocolate with your name on it waiting for you. You can also stop here to pick up gifts for friends and family, like a jar of Vermont’s maple syrup! Check out their website here.



The Billings Farm Museum will be a truly delightful experience. They have an authentically decorated farmhouse and a dairy farm for interactive programs. They also have holiday programs like making historical ornaments and taking wagon rides. This farm is a scenic stroll from Woodstock's center and is considered one of the finest outdoor history museums in the country. Check out their schedule and website here for more information and the different activities they have to offer!


After you have finished your hot cocoa, you can make your way to this small town bookshop, just brimming with coziness, delight, and warmth. It is Vermont’s longest-running independent bookstores, which is quite a feat! Get lost in the collections of vinyl records and various books. You might be surprised by what you find here, and you could come away with a book to read by the fireplace back at your lodgings! Here is their website if you want to get  a glimpse into what it has to offer!

Before another day exploring Woodstock at Christmas time, you can head to Mont Vert Cafe for breakfast. Here you can choose from a great selection of plates like decadent french toast or some hardy biscuits and gravy and pair it with a quality cup of their coffee to feel on top of the world! They use local organic ingredients here and have a welcoming, cozy atmosphere. Please see their website for their menu and hours.


Artisan Park

Artisan Park is a collection of 8 distinct businesses, all located in the same area. This a great opportunity to check out the distillery called Silo Distillery to sample all kinds of spirits, including the holiday ones ;). Then head on over to the Vermont Farmstead Cheese Company. Market and sample their cheeses and specialty foods and gift shop! Harpoon Brewery is also one of the businesses located here, and you can sample some of their quality beers made on-site! For more information about this area here.


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