When autumn paints New England in brilliant shades of red, orange, and gold, there’s no better way to experience the season than with a one-week fall foliage road trip. From winding mountain highways to charming small towns, this itinerary is designed to capture the region’s most iconic fall landscapes.
Over seven days, you’ll travel through Massachusetts, New Hampshire, Vermont, and the Berkshires, exploring a perfect mix of scenic drives, hikes, local foods, and historic towns. Whether it’s your first foliage trip or a yearly tradition, this guide will help you make the most of every moment.
Planning Your New England Fall Foliage Road Trip
Best Time to Catch Peak Colors
The magic of New England’s foliage depends on timing. Generally, late September to mid-October offers the most vibrant colors, with peak arriving earlier in northern states like New Hampshire and Vermont before sweeping south. If possible, aim for the first two weeks of October for the best coverage across the region.
Where to Start and End Your Trip
Most travelers begin in Boston, Massachusetts, thanks to its major airport and easy car rental options. Alternatively, you could start in Portland, Maine or Manchester, New Hampshire, depending on your flight deals. For a seamless loop, Boston remains the most convenient choice.
Rental Car vs. Guided Tour Options
For the freedom to stop at backroad farms, photo-worthy overlooks, and small towns, renting a car is essential. However, if you prefer not to drive, guided foliage tours also depart from Boston and Portland—though they follow stricter schedules.
Packing Tips for a Fall Road Trip
New England weather in fall can be unpredictable. Layering is key—bring a warm jacket, light rain gear, hiking boots, and cozy sweaters. Don’t forget a camera or smartphone with plenty of storage—leaf-peeping moments are endless.
7-Day New England Fall Foliage Itinerary
Day 1: Boston to the White Mountains, NH
- Morning: Arrive in Boston and pick up your rental car. Head north toward New Hampshire’s White Mountains.
- Afternoon: Drive the famous Kancamagus Highway (NH-112), one of the most scenic fall drives in the U.S., with overlooks showcasing rolling mountains blanketed in fiery leaves.
- Stops to Consider:
- Conway Scenic Railroad for a nostalgic train ride through the foliage
- Sabbaday Falls, a short and rewarding hike
- Overnight: Stay in Lincoln or Conway, towns that serve as perfect bases for exploring the White Mountains.
Day 2: Exploring Franconia Notch, NH
- Morning: Start at Franconia Notch State Park, where highlights include the Flume Gorge, a natural canyon with boardwalks winding past waterfalls.
- Afternoon: Take a moderate hike up Artists Bluff for one of the most photographed fall foliage viewpoints in New England.
- Optional Adventure: Weather permitting, drive or take the cog railway up Mount Washington for sweeping 360° mountain views.
- Overnight: Stay near Franconia or Lincoln to enjoy local dining and rest before heading to Vermont.
Day 3: Franconia Notch, NH to Montpelier, VT
- Morning Drive: Cross from New Hampshire into Vermont, known for its covered bridges and maple traditions. The drive itself offers a kaleidoscope of foliage with rolling hills and quaint farmhouses.
- Stops Along the Way:
- Bragg Farm Sugar House – Sample authentic maple syrup and enjoy a maple creemee (Vermont’s version of soft-serve ice cream).
- Covered Bridges – Stop at a few along your route for iconic fall photos.
- Afternoon in Montpelier: Explore the smallest state capital in the U.S. Take a stroll around its historic downtown and visit the Vermont State House, one of the most photographed capitol buildings.
- Overnight: Stay in Montpelier or nearby Waterbury for easy access to the next day’s adventures.
Day 4: Scenic Drives and Small-Town Charm in Stowe, VT
- Morning Adventure: Drive the Smuggler’s Notch (VT-108), a narrow, winding mountain pass that feels like driving through a golden tunnel of leaves.
- Afternoon in Stowe:
- Visit the Von Trapp Family Lodge, with alpine views that inspired The Sound of Music.
- Taste local brews at Stowe’s popular breweries.
- Stop by the Ben & Jerry’s Factory in Waterbury and enjoy seasonal flavors.
- Visit Cold Hollow Cider Mill for fresh cider and warm cider donuts.
- Optional Hike: Sunset at Mount Mansfield, Vermont’s highest peak, provides breathtaking panoramas of fiery foliage.
- Overnight: Stay in Stowe, a town that perfectly blends cozy inns, great dining, and postcard-worthy scenery.
Day 5: Stowe to Woodstock, VT
- Morning in Stowe: If you missed it the day before, take time to explore local art galleries or enjoy a morning walk along the Stowe Recreation Path.
- Drive to Woodstock: The route south passes through winding backroads lined with sugar maples and stone-walled farms.
- Highlights in Woodstock:
- Middle Covered Bridge – A picturesque stop in the heart of town.
- Billings Farm & Museum – Learn about Vermont’s rural heritage and see a working dairy farm.
- Explore local boutiques and cafes in Woodstock’s charming downtown.
- Why Woodstock is Special: It’s often described as one of the prettiest towns in New England, and in autumn, it truly shines with fiery foliage framing its historic homes and green commons.
- Overnight: Stay in Woodstock, where you’ll find cozy inns and B&Bs that capture the essence of small-town New England.
Day 6: Southern Vermont to the Berkshires, MA
- Morning Drive: Leave Woodstock and head south toward Massachusetts, where the Berkshires await with rolling hills and artistic flair. The transition from Vermont’s rugged peaks to the Berkshires’ gentle valleys makes for a scenic journey.
- Stops Along the Way:
- Chesterwood in Stockbridge – Former home and studio of sculptor Daniel Chester French, surrounded by beautiful gardens.
- Norman Rockwell Museum – A must-visit for classic American art lovers.
- Afternoon Hike: Climb Monument Mountain for panoramic views of the Housatonic Valley, especially stunning in peak foliage.
- Evening in Great Barrington or Lenox: Enjoy a cozy dinner in one of these lively towns, known for their farm-to-table restaurants and cultural history.
- Overnight: Stay in the Berkshires to fully embrace the artsy, laid-back vibe of the region.
Day 7: The Berkshires to Boston
- Morning Stroll: Take one last scenic walk or drive through the countryside before heading back.
- Route Back: Drive east through central Massachusetts, where you may still catch late-season colors.
- Boston Farewell: Return your rental car and wrap up your trip with a relaxing evening in Boston. If time allows, walk the Freedom Trail or enjoy seafood at the historic waterfront before departure.
Travel Tips for Your Fall Foliage Itinerary
Book Early
Hotels, inns, and even campgrounds fill up quickly during peak foliage. Plan your accommodations at least 2–3 months ahead.
Be Flexible
Foliage timing varies from year to year. If your schedule allows, keep your route flexible so you can chase peak colors southward.
Driving Notes
Some roads, like Smuggler’s Notch, are narrow and winding—drive carefully, especially if it’s rainy or foggy.
Budget-Friendly Options
While New England inns can be pricey in October, you can save by booking weekday stays, choosing Airbnbs in smaller towns, or camping in state parks.
Local Food to Try
- Maple syrup treats in Vermont
- Apple cider donuts throughout New England
- Pumpkin-based desserts at roadside bakeries
- Fresh lobster rolls if your trip begins or ends in coastal Massachusetts or Maine
Final Thoughts
One week in New England during the fall is an experience you’ll never forget. From the rugged White Mountains to Vermont’s postcard-perfect villages and the culture-filled Berkshires, this itinerary balances nature, history, and small-town charm. With careful planning and a little flexibility, you’ll enjoy one of the most beautiful seasonal displays in the world—fiery foliage that turns every bend in the road into a masterpiece.
