3 Best Winter Dates in Woodstock, Vermont 

February 25 2024

3 Best Winter Dates in Woodstock, Vermont-  Vermont is one of the New England Region’s most charming states to visit. Woodstock, Vermont provides a wonderful experience with white-steepled churches, restored historic homes, and beautiful scenery, no matter what season you’re visiting. This city is one of the best winter escapes for any couple looking for romance and snowfall. Most tourists and residents find that cozying up to a fire with an adult beverage is quite enough during the winter season, but Woodstock, Vermont has so much more to offer. The Jackson House Inn is one of their few charming bed and breakfasts that exude coziness and romance. However, each of the following date ideas will have most couples racing to throw on their warmest winter attire to go explore. If you can’t figure out what gift to get that special someone this holiday season, consider taking them on a beautiful, serene trip this year in Woodstock, Vermont. 

Here are 3 Best Winter Dates in Woodstock, Vermont

Sugar Bush Farms 
Union Arena 
Vermontology Guided Tours 

Each of these date ideas were chosen based on personal experience, as well as from online reviews. Let’s check out what Woodstock, Vermont has to offer for couples this winter. 

Sugar Bush Farms 

February 25 2024
Image captured from Sugarbush Farm website

Sugar Bush Farms is located on 550 acres of land in central Vermont. Back in 1945, the Ayres family bought Sugar Bush Farms intending to try their hand at country living. The Ayres daughter soon remarried and took over all country living responsibilities under the last name Luce. The Luce’s are the 2nd, 3rd, and 4th generations to live on and tend to this large property. It has always been the Ayres and Luce family’s goal to keep this farm alive and active. Sugar Bush Farms has been called the “Cheese lovers paradise” since its conception and in 1995 this farm took home the blue ribbon for the best-smoked cheese in the country, according to the American Cheese Society. 

During the winter seasons, Sugar Bush expects to get between 70 to 120 inches of snowfall. For travelers with good snow tires, don’t let a few feet of snow stop you from exploring their grounds. When you visit Sugar Bush you can expect to taste test some of their infamous syrups and cheeses. Consider signing up for one of their behind-the-scenes classes too, to learn the ins and outs of producing syrups and the differences between the grades. For all those couples out there looking to tie the knot, Sugar Bush farms also function as a wedding venue. Regardless of your reasoning behind visiting Sugar Bush Farms it is a must-see destination no matter the season of the year. 

Location of Sugar Bush Farms 

591 Sugarbush Farm Road, 
Woodstock, Vermont 05091 
(802) 457- 1757
Sugarbush Farm | Woodstock, VT | Cheese & Maple Syrup Farm

Review of Sugar Bush Farms 

“Such a lovely place. We loved the trail they had. It’s very informational and you see so many beautiful maple trees and even a small white chapel. The tasting room was great. Loved reading and learning about the process of sugar making. Also, everything is dog friendly aside from the tasting room. :) our dogs enjoyed it. Lots of great views as well since you’re surrounded by nature” – Diana S

Union Arena 

February 25 2024
Image captured from Union Arena Community Center website

Union Arena is a non-profit organization located in Woodstock, Vermont. This multi-purpose, four-season community facility is home to some of the best ice skating during the winter and summer months. Union Arena’s mission is to offer affordable and accessible activities for people of all ages, year-round. During the off-season, we can observe cultural activities taking place. Such as theater festivals, graduations, concerts, art shows, and so much more. However, during the chilly months, ice skating is one of the biggest activities taking place.

Ice skating is a great way for couples to fall closer together, literally. The rink is a wonderful way to break the ice in new relationships, seeing as making a fool out of yourself is generally suitable for bonding. For more established couples, ice skating offers a fun, carefree activity that’s prone to get anyone in the Holiday spirit. So grab your nicest hat, warm coat, and gloves, and prepare for an afternoon that you and your partner will never forget.

Location of Union Arena 

80 Amsden Way, 
Woodstock, VT 05091
(802) 457- 2500
Union Arena – Skating in Woodstock, Vermont

Review of Union Arena 

“Great skating rink in Woodstock VT. Reasonable prices and lots of fun.” – Brett M. 

Vermontology Guided Tours 

February 25 2024
Image captured from Vermontology Guided Tours website

Vermontology Guided Tours is a business that leads people of all ages on exceptional tours through Woodstock, Vermont’s most prized establishments and scenery. Each tour is led with at most 6 people, so odds are bonding with your partner may lead to newly formed friendships as well. Vermontology offers 3 tours to choose from, depending on the city you’re in. In Woodstock, you’ll get to pick from 2-day tours and 1 five day tours. 

On the first tour, you’ll see scenic roadways, charming villages, historic locations, and so much more. This tour lasts for around 7 hours, so prepare for a full day of learning and fun. The second tour is for those couples who are of legal drinking age. On the brewery and spirits tour, you’ll visit 3 Vermont breweries, as well as 2 distilleries. Lastly, the third tour requires 5 days of your devoted time. This tour will take you around the state of Vermont to experience amazing attractions and even better flora and fauna. Whether your couples are pre-planners or free spirits, Vermontology Guided Tours offers something enjoyable for everyone. 

Location of Vermontology Guided Tours 

Address: Not currently listed 
(802) 417- 1996
Home | Vermontology Guided Tours

Review of Vermontology Guided Tours 

“Natalia was a pleasure! The tour was great and informative! The sites were beautiful and picturesque!” – Jeanne R. 

Find Your Winter Date in Woodstock, Vermont

Thank you for checking out the 3 Best Winter Dates in Woodstock, Vermont. I hope each of these businesses has inspired you and your partner to take a weekend trip to Vermont’s winter wonderland.

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Lilly Cardoso
Lilly Cardoso
I’m an Interior Design Student at the University of Georgia with a minor in Photography. A large passion of mine has always been creating something, whether in the design, art or writing world that makes an impact on people. My aim with my content is to construct a space that cultivates new ideas for many.

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