10 Best Short Road Trips from Island Pond, Vermont (Essex County)

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10 Easy Road Trips From Island Pond, Vermont: Iconic Things To Do Nearby

If you’re based in Island Pond, Vermont in Essex County and you’re itching to explore beyond your backyard, you’re in a perfect spot. Within about an hour or so, you can reach quiet lakes, covered bridges, mountain views, and small New England towns that feel straight out of a postcard. In this guide, we’ll look at 10 short out-of-county road trips from Island Pond into nearby counties in Vermont and New Hampshire:
  • Caledonia County, VT
  • Orleans County, VT
  • Coös County, NH
  • Grafton County, NH
No Essex County stops, no Island Pond attractions—just new places to explore nearby.

1. St. Johnsbury, VT – Art, History, and a Classic Main Street (Caledonia County)

About a 50-minute drive south, St. Johnsbury is a great “small city” day trip with a little bit of everything. Highlights:
  • Fairbanks Museum & Planetarium – A quirky mix of natural history exhibits, taxidermy, old-school displays, and a small planetarium. It has that “old museum” charm that feels almost like stepping back in time.
  • St. Johnsbury Athenaeum – A beautiful historic library and art gallery. You don’t have to be a book lover to enjoy the old woodwork, paintings, and quiet atmosphere.
  • Walking Main Street – Grab a coffee, browse local shops, and admire the older brick buildings.
You can easily spend half a day here wandering between the museum, the Athenaeum, and a café or two. If you’ve been craving more “civilization” after time in the woods, this is a nice balance.

2. Kingdom Trails & Burke Mountain – Biking and Views (Caledonia County)

Head about an hour southwest to the Burke / East Burke area, famous for its Kingdom Trails and mountain views. What to do:
  • Kingdom Trails – Miles of trail networks ideal for mountain biking. They range from gentle, rolling options to more technical rides. If you don’t bike, some sections work well for hiking, too.
  • Burke Mountain – Drive up the Burke Mountain Auto Toll Road (in season) for big views without a big hike. On a clear day, it feels like you can see half of Vermont.
  • Village of East Burke – A small but lively spot with bike shops, casual food, and that classic “outdoor town” feel.
If you love the outdoors near Island Pond but want a slightly different scene, Burke is a natural next step.

3. Lake Willoughby – The Fjord-Like Gem of Vermont (Orleans County)

Less than an hour west, Lake Willoughby in Westmore might be the most dramatic lake in Vermont. It’s long, deep, and framed by steep cliffs that make it feel almost like a mini fjord. Things to enjoy:
  • Beach Time – There are public beach areas on the north and south ends. Pack a blanket, some snacks, and enjoy a slow afternoon by the water.
  • Hiking Nearby Peaks – Trails on Mount Pisgah or Mount Hor give you big views out over the lake. Some sections are steep, but the payoff is huge.
  • Scenic Driving – Even just driving along the lake with the windows down feels special, especially in fall when the leaves explode in color.
If you’ve ever wished for a lake that feels both wild and peaceful, this is it.

4. Newport, VT – Lakeside Strolls & Border Vibes (Orleans County)

Around 45–50 minutes northwest, Newport sits on the southern shore of Lake Memphremagog, a long lake that stretches up into Canada. What to check out:
  • Boardwalk & Waterfront – Stroll by the lake, watch the boats, and enjoy the open view across the water.
  • Lake Memphremagog Cruises (seasonal) – If available, a boat tour gives you a new angle on the area.
  • Downtown Shops and Cafés – Small-town Vermont at its finest: local food, friendly people, and relaxed pacing.
I once spent a rainy afternoon right on the waterfront here, watching clouds move over the lake. Even in bad weather, it felt peaceful.

5. Jay Peak Resort – Adventure in Every Season (Orleans County)

About an hour and 15 minutes from Island Pond, Jay Peak is known for big snow in winter—but it’s worth the drive in every season. Why go:
  • Skiing & Snowboarding – In winter, Jay is a powder magnet with terrain for beginners and experts.
  • Jay Peak Pump House Indoor Waterpark – Slides, a lazy river, wave pool, and hot tubs. Great for families or anyone who wants a break from the cold or rain.
  • Scenic Rides & Hiking – In summer and fall, explore trails or ride up for views of the surrounding mountains.
If you’re craving more action than a quiet hike, Jay Peak brings the energy—especially for kids and teens.

6. Littleton, NH – Classic New England Main Street (Grafton County)

Head southeast for about an hour and you’ll find yourself in Littleton, New Hampshire, a cheerful small town set along the Ammonoosuc River. Don’t miss:
  • Downtown Main Street – Lined with shops, bookstores, and restaurants. It’s the kind of place where you actually enjoy “just walking around.”
  • Riverwalk Covered Bridge – A pretty covered bridge and river walk that makes a nice photo-op and short stroll.
  • Pollyanna Statue – A fun, quirky nod to author Eleanor H. Porter, who grew up here. It’s a quick stop but adds character to your visit.
Littleton is perfect when you want a day of casual exploring, coffee, and window-shopping.

7. Franconia Notch State Park – Big Mountain Scenery (Grafton County)

Roughly 1 hour and 15 minutes south of Island Pond, Franconia Notch State Park sits in the heart of New Hampshire’s White Mountains. Top experiences:
  • Flume Gorge – A well-maintained trail and boardwalk take you through a narrow gorge with waterfalls, covered bridges, and towering rock walls. It’s popular, but for good reason.
  • Cannon Mountain Aerial Tramway – Ride the tram to the summit of Cannon Mountain for huge views without the uphill hike.
  • Scenic Pull-Offs – Even just driving through the notch feels special, especially in fall.
If you’ve ever wanted a simple way to feel “deep in the mountains” without a long trek, this is your spot.

8. Bretton Woods & Mount Washington Views (Coös & Grafton Counties)

About 1.5 hours from Island Pond, the Bretton Woods area and the surrounding Presidential Range deliver classic New Hampshire scenery. What to see and do:
  • Views of Mount Washington – On clear days, the tallest peak in the Northeast looms in the distance. Even from the valley, it’s impressive.
  • Bretton Woods Ski Area – In winter, it’s all about skiing and snowboarding with wide, friendly trails.
  • Scenic Drives – The stretch of Route 302 through here is one of the prettiest drives in the region.
If you’ve ever wanted a “mountain resort” feel without flying out West, this is a nice taste of it.

9. Santa’s Village – A Wholesome Family Day (Coös County, NH)

About an hour and 20 minutes from Island Pond, in Jefferson, NH, you’ll find Santa’s Village, a Christmas-themed amusement park that’s surprisingly charming even for adults. Why it’s worth the trip:
  • Kid-Friendly Rides – Gentle coasters, water rides, and themed attractions for younger families.
  • Christmas Atmosphere – Carols, festive decorations, and Santa himself (even in summer). It’s like stepping into a holiday movie.
  • Comfortable Size – Big enough to fill a day, small enough to not feel overwhelming.
If you’re traveling with kids or grandkids, this might be their favorite road trip on the list.

10. Lancaster, NH – Covered Bridges and Country Roads (Coös County)

A little over an hour southeast, Lancaster is a laid-back small town with a nice mix of scenery and quiet charm. Things to enjoy:
  • Covered Bridges – Seek out local covered bridges for photos and short walks. They’re little slices of classic New England you can actually drive through.
  • Village Green – Relax on the town green, grab an ice cream or coffee, and soak in the small-town feel.
  • Scenic Country Roads – The roads into and around Lancaster are perfect for an unrushed Sunday drive.
If you like simple pleasures—views, bridges, and quiet streets—this is a nice, low-key day trip.

Tips for Planning Your Road Trips From Island Pond

To make these short road trips from Island Pond smoother, keep a few basics in mind:
  • Check drive times – Most of these are within 45 minutes to 1.5 hours. Pick what fits your energy level for the day.
  • Watch the seasons – Some attractions (like waterparks or auto roads) are seasonal, and winter weather in the Northeast can change fast.
  • Pack simple extras – A light jacket, water, and some snacks go a long way, especially if you end up on a trail or at a lake longer than planned.
  • Fill up the tank – Once you leave town, gas stations can be a bit spread out, especially on the more rural routes.

What’s Your Favorite Day Trip From Island Pond?

Living in or visiting Island Pond, VT means you’re surrounded by easy road trip options across Caledonia County, Orleans County, and into Coös and Grafton Counties in New Hampshire. From lakes and mountains to museums and small-town main streets, you can pick a new direction every weekend and still find something fresh. Have you taken any of these drives yet? Which stop would you choose first—Lake Willoughby, St. Johnsbury, or maybe Littleton? Share your thoughts in the comments—and if you know someone in northern Vermont or New Hampshire looking for easy getaway ideas, please share this post with them. Your tips and stories can help other travelers discover their next favorite road trip from Island Pond.
Location: Georgetown, IN, USA

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