Winter Weekend Getaway: Jamaica, Vermont Itinerary (Snowmobiling, Horseback Riding & Gear Tips)

Amber in New England
Nov 24, 2021
4 min read

Updated: 15 hours ago

Amber in New England | Updated Mar 18, 2023

Looking for somewhere in New England to spend a weekend this winter? Tired of the usual ski‑town rut?

How about a weekend in Jamaica, Vermont. Yes, that Jamaica, tucked away in the west end of the Green Mountain National Forest. This quiet little town is packed with winter‑friendly activities, and offers a perfect mix of cozy cabin vibes and outdoor fun.

sunset photo in jamaica, vermont while on a weekend vacation

Day 1: Arrival, Cabin Time & Local Provisions

We headed out mid‑morning for our drive north and made a lunch stop in Wilmington, Vermont. Note: One of the spots we featured previously, Jezebel’s Eatery, appears to be permanently closed as of 2024. So instead, consider grabbing lunch or a snack at a local café or pub in Wilmington and check signage ahead of time.

We arrived at our cozy little cabin along the river (tiny, wooden, and super‑relaxed). On the kitchen table: a hand‑drawn map of the area (because yes, there was basically zero cell service). A few dirt‑road miles in brought us to D&K’s Grocery, however the store has been replaced and the new go‑to is West River Provisions at 3816 VT‑30 in Jamaica. Friendly staff, good selection of snacks, deli items and local craft beer.

Back at the cabin we made tacos (my favorite group dinner), cracked open our craft selections, played card games at the kitchen table and plotted our weekend.

Tip: Bring all your supplies, as nearby stores are limited and winter road/parking conditions can slow you down.

Day 2: Horseback Riding + Waterfall Walk + Relaxation

Morning: We bundled up in layer upon layer (seriously, winter in Vermont does not mess around) and drove about an hour north to Mountain View Ranch in Danby. They offer year‑round guided horseback rides; our guides matched each of us with a horse based on skill and confidence. It was my first time riding in winter: the woods, the open field, the mountains in the background, all worth the frost‑bite.

Gear moment: Since we were mostly moving slowly on horseback, staying warm without bulk mattered. I relied on a well‑fitted mid‑layer fleece that traps heat but doesn’t feel bulky under the riding jacket. (Fleece guide)

Afternoon: On the way back we stopped at Pike Falls, a short forest trail to a partly frozen waterfall. Stunning. But the icy walk was slippery, and a few of us admitted to some awkward tumbles. Definitely bring micro‑spikes or good traction boots, and treat each step like you’re tip‑toeing on glass.

Gear moment: Since walking on icy terrain means sweat + cold = no fun, a good moisture‑wicking base layer is non‑negotiable. (Base‑layer guide)

Evening: Back at the cabin, we cooked together, relaxed, and soaked in the river‑view winter charm.

Day 3: Snowmobiling & Scenic Drive Home

We ventured out to Snowmobile Vermont - Killington•Okemo Mountain Tour for a guided one‑hour snowmobile tour. My first time riding one, and it was exhilarating: zooming through trails under ski‑lifts, pit‑stopping for photos under the hills.

waterfall on vacation in jamaica, vermont

Then it was time to hit the road back home — already planning “Can we do it again next winter?”

Bonus: Winter Hike Option & Gear‑Friendly Activity

Even though I didn’t do a full hike on this trip, Jamaica and the surrounding area offer some excellent winter‑friendly trails that are perfect for snowshoeing, cross‑country skiing, or a quiet snow‑covered stroll. One of my personal favorites is Jamaica State Park. Its 772 acres of woodland are beautiful in the winter, with trails groomed for cross‑country skiing and plenty of space for snowshoeing. Add micro‑spikes or snow‑shoes, and you’ve got yourself a peaceful, snow‑blanketed trail to explore.

Other nearby trails worth checking out include:

Putney Mountain - Over 26 miles of trails winding through the forest, home to Vermont’s second-largest Ash tree.
Bromley Mountain - A 6.2‑mile trail that’s also part of a ski area, giving you options for both hiking and winter sports.
Bald Mountain - Offers three different trail options to the summit, perfect for a shorter winter hike or snowshoe adventure.

Pro tip: If you plan to hike or snowshoe in this area, gear up with a reliable moisture-wicking base layer, a warm mid-layer fleece, a waterproof outer layer, good winter boots, and traction devices or snow‑shoes. Layering properly makes all the difference when exploring snowy Vermont trails.

snowboarding on mount killington while on vacation in jamaica, vermont

What You’ll Want to Pack / Gear Focus

Winter in Vermont can be beautiful, but it can also be brutally cold if you’re not prepared. Here’s what I recommend bringing to stay warm, comfortable, and ready for any adventure:

Moisture‑wicking base layer – A must for hikes, waterfall walks, or any activity where you might break a sweat. Staying dry keeps you warm and happy.
Mid‑layer fleece – My go-to for more stationary winter activities like horseback riding or standing on a snowy trail. Traps heat without adding bulk.
Waterproof and insulated outer jacket + pants – Essential for snow, sleet, or icy winds. Look for something breathable so you don’t overheat while moving.
Footwear – Your feet must stay dry. You are sitting in the snow and exposed to wind. Standard hiking boots often don't cut it. I highly recommend a dedicated winter boot with at least 400g of insulation and a high ankle. Check out my review of the 10 Best Women's Hiking Boots, where I test several models specifically for deep snow and extreme cold.
Warm accessories – Gloves, hat, scarf, or a buff. Trust me, the Vermont wind will find you.
Optional gear – Snow‑shoes or traction devices are perfect for exploring Jamaica State Park or other snowy trails.
Cabin essentials – Snacks, craft beer, card games, and a map or offline GPS. Service is spotty in this area, so come prepared.

Layering properly and packing smart will make all the difference in enjoying your winter weekend, whether you’re hiking, snowmobiling, or just cozying up in your cabin.