10 Unforgettable Short Road Trips from Winooski, Vermont

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10 Easy Road Trips Near Winooski, Vermont (That Take You Out of the County)

If you’re based in Winooski, Vermont and you’re itching for a quick escape, you’re in luck. Within about an hour or two, you can find mountain lakes, historic towns, island drives, and even a quick hop over to New York State—without needing a full vacation week. Below are 10 short out‑of‑county road trips from Winooski that tap into the best of nearby counties like Addison, Franklin, Grand Isle, Lamoille, Washington in Vermont, plus Clinton and Essex Counties across the lake in New York. Each trip is close enough for a day out, but fun enough to feel like a little adventure.

1. Island-Hopping on Lake Champlain – Grand Isle County, VT

Want a drive that feels like a mini coastal vacation without leaving Vermont? Head north and west from Winooski and explore the Lake Champlain Islands in Grand Isle County. You’ll cross causeways and bridges with water on both sides, pass farm stands, and find quiet state parks where you can unpack a picnic. Highlights:
  • Grand Isle State Park – Great for lakeside walks, picnics, and swimming in summer.
  • Sand Bar State Park – Long sandy beach, shallow water, perfect for kids on a hot day.
  • Local farm stands and creemee (soft-serve) stops along Route 2.
If you like slow, scenic drives, this is a perfect Sunday afternoon trip. Bring a camp chair, a cooler, and watch the sunset over the Adirondacks across the lake.

2. Crossing the Lake to Plattsburgh – Clinton County, NY

From Winooski, you’re surprisingly close to New York. Just drive to the ferry dock in Burlington or Charlotte and cross Lake Champlain to **Clinton County**. Once you land near Plattsburgh, you’ll find a laid‑back small city with lake access, local food, and some quiet history. Things to do in and around Plattsburgh:
  • Stroll around Plattsburgh’s downtown for coffee shops, local restaurants, and small boutiques.
  • Relax at a Lake Champlain beach—bring a towel and a book.
  • Check out area historic sites related to the War of 1812 if you’re a history buff.
The ferry ride itself is half the fun. On a clear day, you’ll get great views of both the Green Mountains and the Adirondacks.

3. Adirondack Escape to Keeseville & Ausable Chasm – Essex County, NY

If you’re up for a slightly longer outing, head across the lake into Essex County, New York, and explore the rugged edge of the Adirondacks. One standout stop is Ausable Chasm, sometimes called the “Grand Canyon of the East.” Why go:
  • Walk along the rim trails with sweeping views into the chasm.
  • Try guided rafting or tubing in season for a bit of adventure.
  • Explore the small town of Keeseville for a low‑key local feel.
If you enjoy dramatic rock formations and the sound of rushing water, this road trip from Winooski feels like a totally different world, yet it’s still doable as a day trip.

4. Classic College-Town Vibes in Middlebury – Addison County, VT

Just south of Winooski lies Addison County, home to the charming town of Middlebury. It’s one of those places where you park the car and just wander. What to do:
  • Walk around Middlebury College’s pretty campus and enjoy the open green spaces.
  • Explore downtown Middlebury with its shops, cafés, and river views.
  • Visit nearby covered bridges and quiet back roads for scenic photos.
Middlebury has a relaxed, intellectual feel that’s perfect for a slower-paced day. If you love bookstores, coffee, and casual strolls, this is your spot.

5. Farm Country & Lake Views Around Vergennes & Ferrisburgh – Addison County, VT

Another great Addison County road trip from Winooski is toward Vergennes and the surrounding countryside near Lake Champlain. Vergennes calls itself Vermont’s smallest city, but it packs in a lot of charm. Ideas for the day:
  • Walk around Vergennes’ compact downtown and grab a bite at a local restaurant.
  • Drive out toward Button Bay and surrounding back roads for big sky and farm views.
  • Stop at farm stands for fresh produce in late summer and fall.
This is an easy drive with wide-open views—ideal if you just need to roll the windows down and decompress.

6. Small-Town New England Charm in Stowe – Lamoille County, VT

When people picture Vermont, many of them imagine something that looks a lot like Stowe in Lamoille County. From Winooski, you can head east and a bit north to reach this mountain town that truly shines in every season. What you can do in Stowe:
  • Walk or bike the Stowe Recreation Path for easy, scenic views.
  • Browse Stowe’s village for galleries, shops, and cafés.
  • Drive up toward the Mountain Road area for sweeping views of Mt. Mansfield.
In winter, Stowe is a ski hub. In fall, it’s a foliage favorite. But even in mud season or mid‑summer, it still has that postcard feel.

7. Waterbury & the Green Mountain Gateway – Washington County, VT

For a classic Vermont day trip from Winooski, point the car toward Waterbury in Washington County. The town sits at a crossroads for many Green Mountain adventures. How to enjoy the day:
  • Explore downtown Waterbury’s restaurants and shops.
  • Drive scenic back roads and soak in mountain views.
  • Use Waterbury as a jumping‑off point to nearby hiking areas and reservoirs.
If you’re the kind of person who likes a mix of small-town exploring and short drives to nature, Waterbury makes a great base for the day.

8. Capital Day in Montpelier – Washington County, VT

From Winooski, it’s an easy trip to Montpelier, the state capital and a highlight of Washington County. It’s the nation’s smallest state capital, and that’s a big part of its charm. Things to see and do:
  • Walk by the Vermont State House and admire its gold dome.
  • Explore downtown streets lined with bookstores, cafés, and independent shops.
  • Take a short walk along the river or nearby neighborhood streets for that classic New England feel.
Montpelier has a relaxed, community vibe. It’s a great spot if you like your cities small, walkable, and friendly.

9. Rural Escape to Enosburg & Franklin County Back Roads – Franklin County, VT

If your idea of a perfect road trip from Winooski is more about quiet fields than busy sidewalks, head north into Franklin County around places like Enosburg. This is where Vermont shows off its farm country side. Why you might like it:
  • Drive through rolling farmland with wide views and old barns.
  • Stop in small villages for a snack, a coffee, or a quick walk.
  • Enjoy a slower pace—this area feels a world away from busy highways.
If you’re into photography, these back roads are full of classic Vermont scenes, especially around sunrise or sunset.

10. Quiet Lakes and Forests Near Island Pond & Beyond – Essex County, VT

For a deeper retreat into the Northeast Kingdom feel—while still keeping it realistic for a long day trip from Winooski—head toward the more remote parts of Essex County, Vermont. Areas around small lakes and forested roads give you that “off the grid” energy, even if you’re only gone for the day. What to expect:
  • Plenty of quiet forest roads and small lakes to pull over and enjoy the view.
  • Opportunities for short walks, birdwatching, and simply breathing fresh air.
  • Fewer crowds than you’ll find in more popular Vermont destinations.
If you’re craving quiet and don’t mind a bit more driving, this kind of trip can really reset your mind.

Tips for Enjoying These Winooski Road Trips

To make the most of these day trips from Winooski, keep a few simple tips in mind:
  • Check the season: Some roads, parks, or attractions are seasonal. Fall foliage, winter snow, and spring mud all change how each place feels.
  • Pack basics: Water, snacks, a light jacket, and maybe a blanket for impromptu picnics.
  • Leave time to wander: The best part of Vermont and upstate New York drives is often the unplanned stops—farm stands, viewpoints, and back-road detours.
Think of these trips as starting points. Each county—Addison, Franklin, Grand Isle, Lamoille, Washington, Clinton (NY), and Essex (NY/VT)—has layers you can explore over multiple weekends.

Where Will You Go First?

Living near Winooski (or visiting it) puts you in an amazing spot. In less than an hour or two, you can:
  • Island-hop across Lake Champlain
  • Stroll through classic Vermont towns like Stowe and Middlebury
  • Cross into New York for Adirondack scenery
  • Enjoy quiet farm roads and forest lakes
Which of these 10 short road trips near Winooski sounds most like your style—mountains, lakes, small towns, or back roads? Share your thoughts in the comments—and if you’ve discovered a hidden gem in any of these counties, I’d love to hear about it. If you found this guide helpful, please share it with a friend or family member who’s planning a Vermont getaway or looking for easy weekend trips from Winooski. The more ideas we swap, the better our next road trips will be.
Location: Georgetown, IN, USA

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