A girls weekend getaway in Vermont hits differently in October. The Deerfield Valley turns gold and red around West Dover and Wilmington, the crowds thin out on weekdays, and a farmhouse built for a crowd means nobody is splitting a hotel room or hunting for a second Airbnb down the road. If you are planning a fall trip with your closest friends, here is how to build a weekend around wine, shopping, a spa afternoon, and a house with enough space for everyone to actually relax together.
Morning: Coffee, Foliage, and a Slow Start
Start slow. Vermont mornings in October run cool, often in the 40s, so a fire in the kitchen and coffee on the porch before anyone gets moving is part of the appeal. When the group is ready, a short drive on Route 100 or a stop at one of the overlooks covered in our fall foliage guide gets everyone out of the house and into the color before the day fills up. Nobody needs a full itinerary before lunch — that is the point of staying somewhere with a pond, a hiking trail, and a hot tub instead of a hotel corridor.
Afternoon: Wine Tasting and Wilmington Shopping
Wilmington’s Main Street is built for a slow afternoon with friends. Start with the shops — Bartleby’s Books for something to read by the fire pit later, plus the boutiques and gift shops covered in our Wilmington shopping guide — then head out to Honora Winery & Vineyard in nearby Jacksonville for a tasting. If your group wants to make a full afternoon of it, our fall beverage trail lays out a few more stops between wineries, breweries, and a distillery tasting room, all within a short drive of downtown.
Late Afternoon: A Spa Treatment at Serenity Spa
For a group that wants an actual spa afternoon rather than just a scenic drive, Serenity Spa keeps a location downstairs at the Crafts Inn on Main Street in Wilmington, with massage, body work, and facial treatments plus access to the inn’s pool, hot tub, and saunas. It is by appointment, and October weekends book up, so call ahead if you want the whole group scheduled back to back. It is an easy add to a wine-and-shopping day since it sits right in the same few downtown blocks.
Evening: Hot Tub, Fire Pit, and Good Company
This is where a big farmhouse earns its keep. Eight bedrooms and five bathrooms means nobody is waiting in line before dinner, and the group can actually spread out instead of stacking up in one shared hotel suite. Soak in the hot tub, build a fire outside, and let the game room handle whatever competitive energy is left after a day of wine tasting. The pond and the private trail are there too if anyone wants a quiet walk before bed — October evenings are crisp enough for a fire but rarely too cold to be outside for a while first.
Planning Your Fall Girls’ Weekend Getaway
The tightest weekend on the fall calendar is Columbus Day, October 9 through 12, 2026 — read our Columbus Day weekend guide for why that particular stretch draws the biggest crowds and the highest demand for lodging. If your group can be flexible, the weekends on either side of it tend to have similar color with more availability and lower rates. Either way, a group of eight or more books out fast in a farmhouse this size, so lock in dates a few months out rather than a few weeks out — our guide to booking a fall foliage trip covers the timing in more detail.
🗺️ More to Explore Near Mount Snow
- Columbus Day Weekend in Vermont — the highest-demand fall weekend and how to plan around it
- Vermont Fall Beverage Trail — wineries, breweries, and a distillery tasting room near Mount Snow
- Downtown Wilmington Walking Tour — shops, cafes, and galleries within a few blocks of Main Street
- Vermont Fall Wedding Weekend — how a group of 15-20+ uses the house for a bigger event
- Fall Guys’ Weekend Getaway — the itinerary built for the other half of your friend group
Frequently Asked Questions
What is the best time in October for a girls weekend
Frequently Asked Questions
What is the best time in October for a girls weekend in Vermont?
Foliage around West Dover and Wilmington typically runs from late September through the third week of October, with peak color usually landing in the back half of the month. Columbus Day weekend (October 9-12, 2026) is the single busiest stretch, so book it early or aim for a quieter weekend just before or after if you want more flexibility on dates.
Do we need reservations for wine tasting or the spa?
Reservations are recommended for both, especially on fall weekends. Call ahead for a Serenity Spa appointment if you want the group scheduled together, and check Honora Winery’s current hours before you go since tasting room schedules can shift seasonally.
How many people can stay at the house?
Valley View Villa has eight bedrooms and five bathrooms and comfortably sleeps a large group, which makes it a good fit for a girls weekend where everyone wants their own space rather than sharing a hotel room.
Is Wilmington within walking distance of the wineries and breweries?
Downtown Wilmington shopping and dining are walkable on Main Street, but the wineries, breweries, and distillery on the fall beverage trail are a short drive apart, not a walking loop, so plan on driving (or designating someone) between stops.
What else is there to do if it rains?
A rainy day is exactly when the house’s game room, hot tub, and fireplace earn their keep. Downtown Wilmington’s shops, bookstore, and cafes are also entirely indoors if the group wants to get out of the house for a few hours.
