Arrival in Boston
Arrive in Boston and pick up a hire car
This trip runs one way, from Boston up to the Maine coast, so book a one-way hire car (pick up in Boston, drop off at Portland International Jetport) rather than a return, which saves a long backtrack on the last day. Foliage timing shifts every year and moves from north to south and high ground to low: the Green and White Mountains are often near peak in late September to early October, while the Maine coast usually peaks in mid-October, so check a live foliage tracker for the current year before you fix your dates. Book flights →
Check in near the North End or Back Bay
Base yourself centrally for one night only. You will not need the car in the city, so find it a parking spot and leave it there until tomorrow. Search hotels →
Guided walking tour of the Freedom Trail
A guided walk is the easiest way to make sense of Boston's compact, tangled old core in one afternoon, threading from the Common through the Financial District and into the North End, with a guide filling in the history you would otherwise walk straight past. Search walking tours in Boston on GetYourGuide →
Dinner in the North End
Boston's Italian North End is dense with family-run trattorias; walk until you find one busy with locals rather than chasing a specific name, and leave room for a cannoli from one of the neighbourhood's old bakeries afterwards.
North to Vermont: Quechee Gorge and Woodstock's covered bridges
Drive from Boston to Quechee, Vermont
It is about 140 miles, roughly two and a half hours, up I-93 and I-89 to White River Junction, then west into Vermont. Break the drive up rather than rushing it; there is no need to be in Vermont before lunch.
Quechee Gorge and Simon Pearce
Quechee Gorge is a 165-foot-deep ravine cut by the Ottauquechee River, viewed from the road bridge or a short trail down to the water. A few minutes away, Simon Pearce's glassblowing workshop sits over the river by an old dam; you can watch glassblowers at work and get lunch on the terrace above the falls.
Check in in Woodstock
Woodstock, ten minutes further on, is the picture-postcard Vermont village this trip is built around: a green, a church spire, and white clapboard houses. Check in and leave the car; the village and its bridges are all walkable. Search hotels →
Covered bridges of Woodstock
Walk to the Middle Bridge, just past the Village Green and rebuilt in 1969 by master bridgewright Milton Graton, then drive or cycle the couple of miles east to the Taftsville Covered Bridge, completed in 1836 and one of the oldest working covered bridges in the country. Both cross the Ottauquechee and are at their best with the hillside behind them turning colour.
Apple picking at an orchard near Woodstock
Vermont has several pick-your-own apple orchards within a short drive of Woodstock, most open through October with cider, cider doughnuts and fresh-pressed juice alongside the picking. Hours and picking conditions vary through the season, so it is worth calling ahead or checking their site before you go. Search apple orchard tours in Woodstock on GetYourGuide →
Vermont Route 100: covered bridges, cider and the Green Mountains
Drive north on Vermont Route 100 to the Mad River Valley
Route 100 is Vermont's classic north-south scenic road, running the length of the Green Mountains through small towns rather than along an interstate. The direct drive from Woodstock to the Mad River Valley (Warren and Waitsfield) is under an hour and a half, but budget the whole morning; this is a road for stopping, not covering ground quickly.
Warren and Waitsfield covered bridges
The Mad River Valley has two well-known covered bridges a few minutes apart: the Warren Covered Bridge, built in 1880 and set right against the river below the village, and the Great Eddy (Waitsfield) Covered Bridge from 1833, one of the oldest in the state. Both are an easy stop, and Warren's small village centre is worth a wander.
Lunch in Waitsfield
Waitsfield has a handful of good, unfussy lunch spots along Route 100; this is the last easy meal stop before the drive continues north.
Cold Hollow Cider Mill, Waterbury Center
Cold Hollow is one of Vermont's best-known cider mills, pressing on a traditional rack-and-cloth press and known for its cider doughnuts; it is a working mill and shop rather than a polished visitor attraction, open daily. It sits directly on the route north to Stowe. Search cider tours in Waterbury on GetYourGuide →
Stowe Gondola SkyRide
The gondola at Stowe Mountain Resort runs daily through mid-October, climbing towards the summit of Mount Mansfield, Vermont's highest peak, for a panoramic view over the Green Mountains that is hard to beat for foliage. It gets busy on clear afternoons in peak season, so aim for later in the day when the light is better anyway. Check current-year operating hours before you go, as the season end date can shift with the weather.
Check in in Stowe
Stowe is a proper mountain town with plenty of choice for dinner after a long day on the road. Search hotels →
Into New Hampshire: Franconia Notch and the Kancamagus Highway
Drive from Stowe to Franconia Notch, New Hampshire
It is about 80 miles and close to two hours, east across northern Vermont and then south into New Hampshire on I-93. This is the trip's other big driving day, so get moving in good time; there is a lot to see before you reach North Conway tonight.
Franconia Notch: the Flume Gorge
Franconia Notch State Park sits right on I-93, and the Flume Gorge is its signature stop: an 800-foot natural granite gorge reached by a two-mile boardwalk loop that climbs alongside the rushing water. It stays open into late October in 2026, so it fits the foliage window, but admission is by timed ticket, so book online in advance rather than counting on a walk-in slot; allow an hour to an hour and a half for the loop. Note that Cannon Mountain's aerial tramway, the notch's other landmark, is out of service for 2026 while its replacement is planned, so the Flume is the stop to make.
Lunch in Lincoln
Lincoln, at the western end of the Kancamagus Highway, has straightforward lunch options and is the last real town before the road climbs into the White Mountain National Forest.
Kancamagus Highway: Sabbaday Falls and Albany Covered Bridge
The Kancamagus (NH-112) runs 34.5 miles through the White Mountain National Forest with no petrol stations or services along the way, so fill up in Lincoln first. Sabbaday Falls is a short, mostly flat half-mile walk to a 45-foot cascade dropping into a green pool, and the Albany Covered Bridge, a short detour off the highway, is one of the most photographed bridges in the state, especially with the Swift River in front of it turning colour.
C.L. Graham Wangan Ground Overlook and Rocky Gorge
The C.L. Graham Wangan Ground Overlook, at the highway's high point of 2,855 feet, gives one of the widest views on the whole route. Further on, Rocky Gorge is a short walk to a narrow granite chute on the Swift River, usually quieter than the bigger stops. Expect the whole drive, with stops, to take three to four hours rather than the roughly hour it would take non-stop.
Check in in North Conway
North Conway, at the eastern end of the Kancamagus, is the base for the next two nights and the natural place for dinner after a long day of driving and short walks. Search hotels →
White Mountains: a foliage hike and the Conway Scenic Railroad
Guided hike up Mount Willard, Crawford Notch
Mount Willard is one of the most rewarding easy-to-moderate hikes in the White Mountains: about three miles round trip, two to two and a half hours, climbing steadily through woods to a ledge with a sweeping view straight down Crawford Notch, one of the most photographed foliage views in the state. Weather at elevation in the White Mountains can turn quickly even on an easy trail, so a guided group is the sensible choice if you are not experienced hillwalkers, and arrive early, as parking at the trailhead fills up fast in foliage season. Search guided hikes in the White Mountains on GetYourGuide →
Lunch in North Conway
Back down and into North Conway village for lunch; the main street has plenty of easy options before the afternoon's train ride.
Conway Scenic Railroad, Valley Train
The Valley Train is an easy hour-long, eleven-mile round trip from North Conway's restored 1874 station through the valley in vintage carriages; it is the simplest way to see the foliage without a hike. If you would rather go further into the mountains, the Mountaineer runs four to four and a half hours on a longer route, but check current-year timetables, as fall schedules and routes can change. Search scenic train rides in North Conway on GetYourGuide →
Echo Lake and Cathedral Ledge
A few minutes from the village, Echo Lake State Park sits beneath Cathedral Ledge, a 700-foot granite cliff. Walk the easy path around the lake, or drive the short auto road to the top of the ledge for a view over the Saco River Valley that is especially good in late-afternoon light.
Dinner in North Conway
An easy last evening in the White Mountains before tomorrow's drive to the coast; North Conway has plenty of choice along the main street.
To the Maine coast: Kennebunkport
Drive from North Conway to Kennebunkport, Maine
It is about 71 miles, just under two hours, southeast out of the mountains and down to the coast. The landscape changes fast on this drive, from forested hills to salt marsh and open sea within the last half hour.
Check in in Kennebunkport
Kennebunkport is a former shipbuilding town turned classic Maine coastal resort, full of Federal and Victorian-era captains' houses. Drop the bags and get straight out to make the most of the afternoon. Search hotels →
Lunch at The Clam Shack
The Clam Shack sits right on the bridge over the Kennebunk River and has served nationally recognised lobster rolls, piled onto a toasted round bun rather than the usual split-top, since 1968. It is takeaway only, eaten at picnic tables over the water, and worth the inevitable queue; note it runs seasonally, roughly May to mid-October, so if you reach the coast at the tail of the foliage window, check it is still open before you count on it.
Dock Square and the village
Dock Square is Kennebunkport's centre, a cluster of shops, galleries and old warehouses at the meeting of Western Avenue, Spring Street and Ocean Avenue. Easy walking, and a good place to browse for an hour.
Cape Porpoise
A couple of miles beyond Dock Square, Cape Porpoise is the quieter working side of Kennebunkport, a real lobstering harbour with Goat Island Lighthouse visible about a mile offshore from the small park at the end of Pier Road. For a closer look, narrated boat tours run out from the harbour and dock briefly at the lighthouse. Search boat tours in Kennebunkport on GetYourGuide →
Portland and departure
Drive from Kennebunkport to Portland
A short run, about 28 miles and 40 minutes up US-1, with the whole morning ahead of you before an afternoon flight.
Portland Head Light, Cape Elizabeth
Completed in 1791 on the orders of George Washington, Portland Head Light is Maine's oldest lighthouse and one of the most photographed in the country, set in Fort Williams Park above the entrance to Casco Bay. Walk the grounds and the small keeper's house museum before heading into the city.
Old Port seafood walking tour
Portland's Old Port is a genuine working waterfront turned into the city's best walking and eating neighbourhood, cobbled streets and old brick warehouses among fishing boats and lobster pounds. A guided food tour is a good way to close the trip out, taking in several stops rather than committing to one restaurant. Search food tours in Portland on GetYourGuide →
Last lobster roll and a wander through the Old Port
Free time to finish with whatever you have not yet had: a last lobster roll, the shops on Exchange Street, or the waterfront itself.
Depart from Portland International Jetport
Return the hire car at the airport, about fifteen minutes from the Old Port, and close out a week of driving with the leaves behind you. Book flights →