I drove this loop the first time in late May because I couldn’t get a decent room anywhere in coastal Maine and decided to just head inland. It turned out to be the best accidental road trip decision I’ve ever made. The White Mountains were still showing snow on the higher peaks, Lake Winnipesaukee was glass-calm in the early morning, and the Vermont farms were putting out their first real green of the year. The leaf-peepers weren’t there. The summer crowds weren’t there. The roads were mine.
That was about 15 years ago, and I’ve run some version of this loop almost every spring since.
Why Do Vermont and New Hampshire Work So Well Together?
These two states are geographically joined at the hip and temperamentally different in ways that make a combined trip more interesting than either one alone. New Hampshire is craggy and dramatic — the White Mountains are the most rugged terrain in New England, and the state has a libertarian streak that shows up in its lack of state income and sales tax. Vermont is softer, more pastoral, politically the opposite, and makes better cheese. Together they give you serious mountains, big lakes, and the full range of New England’s inland landscape.
The drive between them is also surprisingly fast. From Concord, NH to Burlington, VT is under two hours. From North Conway to Stowe is about 2.5 hours via I-93 and I-89. The two states essentially share the Connecticut River as a border and are in constant traffic dialogue with each other through the mountain passes.
The loop I keep returning to:
Boston → Lake Winnipesaukee → White Mountains/North Conway → Franconia Notch → Woodstock, VT → Stowe → Burlington → Mad River Valley → return south through Vermont
Roughly 550 miles total. Four to five days is the sweet spot. You can compress it to three if you’re motivated, or stretch it to a week if you want to hike more.
What Is Lake Winnipesaukee Like in Late Spring?
Lake Winnipesaukee — try saying that fast after the second night — is New Hampshire’s answer to the Great Lakes question. At 72 square miles, it’s the largest lake in the state and big enough that the far shore disappears on overcast days. The town of Meredith on the western shore is the most convenient entry point if you’re coming from the south.
Late May and early June, before the summer cottage season kicks off, is legitimately one of the best times to visit. The lake is still cold for swimming (water temperature in the high 50s), but the surrounding towns have woken up, the marinas are launching boats, and you can get a table at any restaurant without a wait. The drive around the lake on Route 11/Route 109 through Center Harbor, Moultonborough, and Wolfeboro takes about two hours with stops, and the views across the water to the Ossipee Mountains are quietly spectacular.
Wolfeboro is the jewel of the lake — it calls itself the “oldest summer resort in America” (it’s been drawing warm-weather visitors since the 1760s), and the downtown is compact, walkable, and genuinely charming. Lunch at the Wolfeboro Inn’s Wolfe’s Tavern, walk the Cotton Valley Rail Trail along the water, and watch the boats come and go from the town docks. This is exactly the kind of New England lakeside town that people imagine when they imagine New England.
For a night on the lake, the smaller cottage colonies and B&Bs around Center Harbor are more interesting than the larger chain properties in Meredith. Check Expedia filtering for “Lake Winnipesaukee” — the search surface area is wide and some of the small inn properties don’t appear unless you search the specific region.
How Hard Is the Drive Through the White Mountains?
The White Mountains are not a hard drive — but they’re a slow one, and gloriously so. Route 112, the Kancamagus Highway from Lincoln to Conway, is one of the most beautiful mountain roads in the northeastern United States and demands you drive it at 35 mph. In late May the higher sections may still have patches of snow. The Swift River pulls alongside the road for much of its length, and the swimming holes along it (Lower Falls, Rocky Gorge, Sabbaday Falls) are accessible even in shoulder season.
North Conway is the commercial hub and worth a night. It gets a bad reputation from locals who hate the outlet stores, but strip away the strip malls and you have a valley ringed by serious mountains with excellent hiking accessible directly from town. The Cathedral Ledge is a 10-minute drive and the view from the summit (you can drive to the top) across the Saco River valley is jaw-dropping. Attitash Mountain has lift-served mountain biking starting in late May.
Franconia Notch is the mountain experience I’d prioritize if I only had time for one stop in the White Mountains. The notch itself — a narrow glacial pass with mountain walls rising on both sides — is dramatic in any season, but late May has the bonus of waterfalls at full flow from snowmelt. Flume Gorge (a narrow 90-foot-deep glacial chasm with a covered bridge) is one of the genuine natural wonders of New England. Echo Lake for a morning swim is cold but invigorating.
Cannon Mountain Aerial Tramway operates spring through fall and takes you to 4,080 feet in eight minutes. The views from the observation deck extend across Vermont to the Adirondacks on clear days. Worth the $25 tram ticket.
Mountains That Make You Feel Small
Late May in the White Mountains means waterfalls at full force and trails still half to yourself.
What Does the Vermont Side of This Loop Look Like?
Cross into Vermont via I-91 south of St. Johnsbury or take the slower and better Route 2 through Lancaster, NH and Lunenburg, VT. The moment you cross the Connecticut River you notice it — the barns get redder, the roads get more winding, and the hills round out from granite-sharp to something more pastoral.
Woodstock, VT is the first stop I’d make and the most concentrated dose of Vermont village perfection available. The covered bridge on the edge of the green, the brick-and-clapboard main street, the Billings Farm & Museum (a working dairy farm where you can watch cheese being made) — all of it is genuine, not constructed. The town has been wealthy for a long time, which means the historic buildings were never torn down for something cheaper.
The Mad River Valley — home to Waitsfield and Warren, Vermont — is a detour that rewards off-season timing perfectly. Mad River Glen is one of the last ski areas in America with a single chair lift and a “skiers only, no snowboarders” policy. In late spring, the surrounding valley is doing its greening-up routine, the farm stands are opening, and the American Flatbread in Waitsfield is one of the best pizza restaurants in Vermont. It’s a 30-minute detour south of Stowe and worth every minute.
Stowe is the lodgepole of this whole loop. The mountain town is compact and walkable, the restaurant scene is genuinely excellent for a village of 5,000, and the drive up Mountain Road past the church steeple toward Spruce Peak is the most recognizable image in Vermont. In late May, the ski lifts are closed but the resort runs hiking and mountain biking on the lower trails. Stowe Recreation Path runs 5.3 miles along the West Branch River and is the ideal morning walk.
Stay at least two nights in Stowe. The restaurants here require a second dinner: Hen of the Wood is the fine-dining anchor (book well ahead), Piecasso is the best casual pizza in Vermont, and Depot Street Malt Shop is where locals take their kids and out-of-town guests alike.
Burlington and the Lake That Faces the Adirondacks
Lake Champlain at late-spring low crowds is one of New England's most underplayed scenes.
Is Burlington Worth a Full Day?
Yes, and most people give it three hours. Burlington is the largest city in Vermont — which means it has 45,000 people and enough energy to feel like a real city without the scale or cost of Boston. The Church Street Marketplace is the pedestrian main street, genuinely lively with street performers and good independent shops, but the more interesting part of Burlington is the waterfront.
The Burlington Waterfront Park stretches along Lake Champlain with the Adirondacks rising across the water in New York. In late May, the lake is cold and clear and the light off the water in the morning has a quality you don’t get at the coast. Walk or bike the waterfront path, then work back up the hill to the city and have breakfast at Penny Cluse Cafe on Cherry Street — gingerbread pancakes, excellent eggs, the kind of place that earned its reputation.
Shelburne Museum (10 minutes south of Burlington) is the most underrated museum in New England. It’s a 45-acre outdoor museum of American folk art, architecture, and design — 39 buildings from different eras, including a covered bridge moved from its original location, a steamship hauled overland to the grounds, and a lighthouse relocated from Lake Champlain. The collection of quilts, trade signs, and weather vanes is extraordinary. Budget half a day.
What Is the Best Way to Return South?
Route 100 through the spine of Vermont is the answer. This is the most beautiful road in Vermont and possibly in New England — it runs through Morrisville, Stowe, Warren, Waitsfield, Rochester, and south through the Mad River Valley and beyond. The foliage season crowds pack this road in October; in late May it’s quiet, green, and unhurried.
If you’re heading back to Boston, exit Route 100 and pick up I-89 south around White River Junction, then drop down to the Connecticut River valley. If you’re doing a longer loop through more of Vermont, continue south on Route 100 through Weston (best general store in Vermont: Vermont Country Store), Chester, and Grafton.
The drive from Stowe back to Boston via I-89/I-93 is about 3.5 hours without stops. Via Route 100 south to Woodstock and I-89 is about 4.5 hours and significantly more scenic.
Planning this loop around your schedule? The AI Trip Planner can help you sequence the driving days and find the right accommodations along the route. For more detail on individual stops, read our destination guides for Stowe, Burlington, White Mountains, and Lake Winnipesaukee.
For the companion coastal trip, see our New England Lighthouses & Harbor Towns guide — the two trips pair well as a two-week New England circuit.