10 Easy Road Trips from Killington Village, VT (Without Leaving the Green Mountains Behind)
If you’re staying in
Killington Village, Vermont and you’ve already hit the slopes, hiked the trails, and sampled the local brews, you might be wondering:
What else is there to do nearby?
The good news: you don’t have to drive far to find totally different vibes, new small towns, and classic Vermont charm. The even better news: all of the ideas below take you
out of Rutland County and into nearby counties like
Windsor, Bennington, Addison (VT), and Washington (NY).
These are short, easy
day trips from Killington Village that you can do in a half day or full day, depending on your pace.
1. Woodstock, VT – Classic New England Charm (Windsor County)
Woodstock is one of those towns that looks like it was built for a postcard. It’s about an hour’s drive east from Killington Village, but the time slips by as you roll past covered bridges and rolling hills.
Why go: It’s the perfect “wander and relax” town.
- Stroll the village green and admire the historic homes.
- Walk across the Middle Covered Bridge for that classic Vermont photo.
- Check out local shops for maple candy, handmade crafts, and cozy sweaters.
On my own visit, I ended up spending almost an hour in a tiny bookstore chatting with the owner about the best local hikes. That’s the kind of place Woodstock is—slow, friendly, and easy to love.
Road trip tip: Park once near the village center and explore on foot. Everything is close together and very walkable.
2. Quechee Gorge – Vermont’s “Little Grand Canyon” (Windsor County)
Just a short drive past Woodstock, you’ll find
Quechee Gorge, one of the most famous natural sights in the state and an easy
half-day trip from Killington.
What to do:
- Walk onto the bridge and look down 165 feet into the gorge.
- Hike the Quechee Gorge Trail down to the river if you want a bit of exercise.
- Check out nearby shops and snack stands for ice cream or a quick bite.
Standing on the bridge, you can feel the wind rush up from the gorge. It’s a little thrilling, even if you’re not afraid of heights.
Timing: You can easily combine Quechee with Woodstock in one day. Spend your morning in Woodstock and head to Quechee in the afternoon for views and a short hike.
3. Manchester, VT – Shopping, Food, and Mountain Views (Bennington County)
Head about 1.5 hours southwest and you’ll reach
Manchester, Vermont, a small town that mixes outlet shopping with mountain-town charm.
Highlights:
- Browse outlet stores and local boutiques along Main Street.
- Visit the grounds of Hildene, the historic Lincoln family estate (even just the outside views are worth it).
- Grab a coffee and people-watch with mountain views in the background.
If you’re traveling with someone who loves to shop and someone who loves the outdoors, Manchester is a great compromise. You can both get what you want in the same day.
Road trip tip: Bring layers, even in summer. Weather in the mountains can change fast.
4. Bennington, VT – Covered Bridges and History (Bennington County)
Drive a bit farther south from Manchester or go directly from Killington Village and you’ll reach
Bennington, a historic town full of Revolutionary War history and quiet backroads.
Don’t miss:
- The towering Bennington Battle Monument (you can see it from around town).
- Several beautiful covered bridges a short drive outside the center.
- Local diners and cafes serving hearty, classic comfort food.
If you like slow drives on narrow country roads with the windows down, this is your spot. It’s easy to pull over, take photos, and just enjoy a slower pace.
Fun idea: Turn it into a “covered bridge hunt” and see how many you can find in one afternoon.
5. Middlebury, VT – College Town with a Creative Side (Addison County)
To the north and west of Killington Village, about an hour and fifteen minutes away, sits
Middlebury, home to Middlebury College and a lively downtown.
Why it’s worth the drive:
- Charming downtown streets with coffee shops, bakeries, and bookstores.
- River views and bridges right by the center of town.
- A relaxed, college-town vibe with a touch of arts and culture.
On my last visit, I grabbed a sandwich from a local deli and found a bench overlooking the river. It wasn’t a big “wow” moment—but it was peaceful, and sometimes that’s exactly what you want from a day trip.
Road trip tip: This is a great spot if you’re craving a quieter, laid-back town that still has good coffee and food.
6. Bristol, VT – Small Town, Big Scenery (Addison County)
Just northeast of Middlebury, Bristol is one of those little Vermont towns that surprises you with how alive it feels, even though it’s small.
What you’ll find:
- A classic main street with shops and spots to eat.
- Views of nearby mountains framing the town.
- A friendly, local feel—don’t be surprised if people say hello as you walk by.
Bristol pairs nicely with Middlebury as a
two-town road trip loop from Killington Village. See both in one day for a fuller taste of Addison County.
Good for: Casual strolling, photography, and grabbing a simple, satisfying meal.
7. Vergennes, VT – Vermont’s Smallest City with Big Character (Addison County)
A bit farther northwest, you’ll reach
Vergennes, known as Vermont’s smallest city. It’s compact, easy to navigate, and surprisingly lively for its size.
Reasons to visit:
- A cozy downtown with restaurants and shops.
- Proximity to scenic spots along the Otter Creek and near Lake Champlain.
- A mix of history and small-city charm, all within a few walkable blocks.
Vergennes is a great choice if you want somewhere that feels different from a ski town, but still has that friendly Vermont feel.
Road trip tip: Consider looping through
Middlebury → Vergennes → Bristol for a full Addison County day trip from Killington Village.
8. Montpelier, VT – The Tiny Capital City (Washington County, VT)
Montpelier, Vermont’s capital, is about 1.5 to 2 hours from Killington Village, depending on your route. It might be the smallest state capital in the country, but it has plenty to see.
What makes it special:
- A striking gold-domed State House that’s hard to miss.
- Walkable downtown with local eateries, bookstores, and coffee shops.
- A laid-back, creative vibe that feels more like a small town than a capital city.
If you’re the kind of traveler who likes to tick off state capitals, this is an easy win. But even if you’re not, Montpelier is worth the drive for its mix of history and everyday life.
Good to know: Parking is usually easier here than in many bigger cities, which makes this a low-stress road trip destination.
9. Cambridge and Salem, NY – Country Roads and River Views (Washington County, NY)
Head southwest from Killington Village and cross into
Washington County, New York for a change of scenery. Towns like
Cambridge and
Salem offer a different kind of rural charm.
What to expect:
- Quiet backroads lined with farms and old barns.
- Small-town main streets with a few cafes and shops.
- Wide-open views that feel very different from the enclosed mountain valleys of Vermont.
This area is perfect if you love to just drive, listen to music, and stop wherever looks interesting. It feels like stepping back in time a bit, in the best possible way.
Road trip tip: Plan a loose route but stay flexible. Part of the fun here is turning down the roads that just “look right.”
10. Hudson River Overlooks & Small Towns (Southern Washington County, NY)
If you keep heading south along the New York side, you’ll find sections of
Washington County that brush up near the
Hudson River, with small towns and country roads that invite slow exploration.
Ideas for your day:
- Look for river overlooks or pull-offs with water views.
- Stop in whatever small town you pass through for a snack or cup of coffee.
- Take side roads that follow the river or climb into the hills for wide-open views.
This kind of road trip isn’t about checking famous sights off a list. It’s about wandering, exploring, and seeing where the day takes you.
Best time: Late afternoon, when the light is soft and the river views are at their best.
Planning Your Road Trips from Killington Village
To keep your day trips smooth and stress-free, here are a few simple tips:
- Check drive times: Most of these are about 45 minutes to 2 hours from Killington Village, one way.
- Fill up on gas first: Some stretches get pretty rural with long gaps between gas stations.
- Pack a light bag: Water, snacks, an extra layer, and a phone charger go a long way.
- Stay flexible: Leave room to stop at that random farm stand or scenic pull-off.
Road trips near Killington don’t have to be complicated. Pick a direction—east to Woodstock and Quechee, west to Middlebury, north to Montpelier, or southwest into New York—and let the day unfold.
What’s Your Favorite Day Trip from Killington Village?
Have you taken any of these
short road trips from Killington Village? Did you fall in love with Woodstock, get dizzy on the Quechee Gorge bridge, or discover a tiny cafe in Washington County, New York?
- Share your own tips in the comments—favorite towns, hidden stops, or scenic drives.
- If you found this guide helpful, share it with friends or family planning a Vermont getaway.
The more we trade stories, the easier it gets for other travelers to find those small, special places just beyond Killington’s slopes.
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