Winter Weekend in Jamaica, Vermont | Travel Itinerary

Updated: Mar 18, 2023

Looking for somewhere in New England to spend a weekend this winter? are you totally over hitting up the usual New England weekend spots? How about Jamaica? No, not the tropical island you're probably imagining, but the one and only, Jamaica, Vermont!. Jamaica is a small, quiet town, tucked away in the west end of Green Mountain National Forest. This area is filled with a ton of different winter activities to please everyone you bring along.

sunset photo in jamaica, vermont while on a weekend vacation

When my husband, a few friends and myself had the opportunity to spend a long weekend in a cabin along the river, we couldn't turn it down. We left mid morning on our journey north and decided to pit stop in Wilmington for lunch. Jezebel's Eatery caught our eye so we went inside and had a seat at the bar. The owner served our meals and we chatted with him about the history of the restaurant. He and his wife were from the U.K. before opening this place. I had a salad with a side bloody mary...since it was vacation. After lunch we stopped in the Village Roost for coffee and snacks to go. Btw their bathroom is really cool 🤷‍♀️

We took off and continued driving to our cabin. It was tiny, wooden, and cozy. On the kitchen table was a hand drawn map of the area, thank god because there was absolutely no service and it was all our first time in the area. A few miles down the dirt road was D&K's Grocery Store where we shopped for food and snacks for the weekend. We probably visited this store ten times throughout our stay, partly because it was the only store in the area and partly because they were SUPER friendly (4.6 stars on Google). They were stocked with your common groceries, a deli in the back, coolers filled with craft beers, and handmade gift items. I would tell you to go but as I'm writing this and looking it up, I see that they are now permanently closed. 😭 Hoping this was for a good reason.

Back to our cabin we went to make tacos, my favorite group dinner...or general dinner, and try our craft selections. We spent the rest of the night hanging around the kitchen table playing card games and planning out the remainder of the weekend.

The next morning we woke up early for our first activity of the day, horseback riding!! We threw on a ton of layers and drove about an hour north to Mountain View Ranch in Danby, where they offer year round guided horseback trail rides. Our horses were hand selected based on our skills and confidence levels. I was super excited with the cutie I got to ride. We rode through a path in the woods and into an open field with the mountains in the back. To say it was freezing is an understatement, but it was totally worth it. I love horseback riding and this was my first time going in the winter. Only about half the group had gone before, so it was a cool activity to introduce to our friends, especially in the winter.

On our way back to the cabin we stopped at Pike Falls, which was a short, lightly walked trail in the woods. Pictures never do justice. This waterfall was covered in ice and so pretty. Be very careful if you plan to visit in the winter, it's hard to see where the ice begins once there is a snow covering. After admiring the waterfall we took the trail back out. The way up was not the easiest and a few of us definitely took a some tumbles getting traction on the hill. As if the falls weren't enough, this short walk was worth it for the laughs. Back to the cabin where we made another group dinner and relaxed before bed. Another fun activity on the horizon!

waterfall on vacation in jamaica, vermont

On day three we traveled a little over an hour to Killington for snowmobiling at Snowmobile Vermont - Killington•Okemo Mountain Tour. This was my first time riding, and I was really excited. We chose the one hour tour and I loved it! We had two guides who we're a lot of fun on the trails. We pit stopped under the ski lifts for some photos before ending the tour and heading home. Can we do it all over again?!

snowboarding on mount killington while on vacation in jamaica, vermont

Although I didn't really hike during this weekend vacation, I was able to try some new activities and thoroughly enjoyed them. There are still a ton of cool places to hike if you do plan to visit, some of the closer options include: