Chasing Fall: The Most Stunning New England Road Trip for Autumn Foliage

There is a particular magic that descends upon New England each autumn. It’s a slow, creeping alchemy that begins in the northern mountains and rolls southward, painting the landscape in a breathtaking tapestry of crimson, gold, amber, and scarlet. For many, witnessing this spectacle is a bucket-list experience, a pilgrimage into the heart of seasonal change. But to truly capture its essence, you need more than just a destination; you need a journey. You need a road trip.

This isn’t just a route; it’s a curated experience, a 10-day odyssey designed to immerse you in the very soul of a New England fall. Crafted from years of personal exploration, local knowledge, and a deep respect for the region’s rhythms, this guide is your key to unlocking the most stunning autumn road trip imaginable. We’ll traverse six states, from the rugged coasts of Maine to the rolling hills of Connecticut, chasing the peak color, savoring local flavors, and creating memories that will glow as warmly as the foliage itself.

The Philosophy of the Journey: Embracing the Unpredictable

Before we turn the key, a crucial piece of wisdom: foliage is a living, breathing phenomenon. It is not a static event. The “peak” is a fleeting, moving target dictated by temperature, sunlight, and rainfall. This itinerary is designed to be flexible, following the typical southward progression of color from late September to mid-October. Your single most important tool is not this article, but the New England Foliage Trackers. Websites like NewEngland.com and state-run tourism sites provide near-real-time updates. Be prepared to adjust your days based on their reports—the chase is part of the adventure.

The Route Overview & Practicalities

Duration: 10 Days, 9 Nights
Approximate Distance: 900-1,000 miles
Best Time to Go: Late September (for the north) to Mid-October (for the south). Aim for the last week of September and the first two weeks of October for the highest probability of spectacular color across the entire route.
Vehicle: Any reliable car will do, but an SUV or a car with good clearance is helpful for potential gravel backroads or mountain ascents.
Booking: Book everything well in advance. Fall is high season, and charming inns, B&Bs, and even hotels fill up months ahead.

Day 1: Arrival in Portland, Maine – A Maritime Prelude

Your journey begins not in the mountains, but by the sea. Portland offers a perfect blend of salty coastal charm and sophisticated urban energy, easing you into the New England vibe.

Afternoon: Arrive at Portland International Jetport (PWM). Pick up your rental car and check into your accommodation. I highly recommend a historic inn in the West End or a hotel within walking distance of the Old Port.
Evening: Wander through the cobblestone streets of the Old Port. The scent of salt air mingles with the aroma from countless restaurants. Indulge in a classic Maine lobster roll—the debate between hot-with-butter and cold-with-mayo is one you must settle for yourself. For an unparalleled culinary experience, make a reservation at Eventide Oyster Co. or Street & Co..
Expert Insight: While Portland itself won’t be at peak foliage, this coastal start allows you to acclimate and provides a stunning contrast between the deep blue Atlantic and the early, muted golds and bronzes beginning to appear in the marsh grasses and shoreline maples.

Day 2: Portland to the White Mountains (North Conway, NH)

Drive Time: ~2.5 hours (not including stops)

Today, we leave the coast and plunge into the heart of New England’s most iconic mountain range.

Morning: Enjoy a hearty breakfast in Portland, perhaps at The Holy Donut (featuring potato-based donuts) or Becky’s Diner for a classic experience. Then, hit the road westward on Route 302. This scenic byway is your gateway to the mountains.
Mid-Morning Stop: Mount Washington Valley. As you cross into New Hampshire, the landscape dramatically shifts. The foothills of the White Mountains rise around you. Your first major stop should be the Conway Scenic Railroad. While you can take a ride, even just viewing the historic 1874 station and the classic steam and diesel locomotives against a mountain backdrop is a photo-worthy moment.
Afternoon: Check into your lodge or B&B in North Conway or neighboring Jackson or Glen. This area is a hub for leaf peepers, with countless shops and outfitters.
Late Afternoon Foliage Fix: Cathedral Ledge. Drive or hike to the top of this granite ledge for a breathtaking, panoramic view of the entire Mount Washington Valley. This is your first true, jaw-dropping vista of the fall colors blanketing the hills and valleys below. The play of light during the “golden hour” before sunset is sublime.
Dinner: Cozy up in a traditional New England tavern. The Red Fox Bar & Grille at the Jackson Resort or May Kelly’s Cottage in North Conway offer hearty meals and local atmosphere.

Day 3: Exploring the Kancamagus Highway

Drive Time: ~3-4 hours for a leisurely, stop-filled journey

Today is dedicated to one of the most famous foliage drives in the world: the Kancamagus Highway (Route 112). This 34.5-mile stretch of road between Conway and Lincoln is a designated National Scenic Byway with no gas stations or commercial development—just pure, unadulterated wilderness.

Morning: Start early with a full tank of gas and a packed lunch from a local deli. Enter the “Kanc” from the Conway side.
Key Stops Along the Kanc:
- Sabbaday Falls: A gentle, half-mile hike leads you to a stunning series of flumes and potholes, where water cascades through narrow granite gorges. The mossy rocks framed by fiery foliage are a photographer’s dream.
- Lower Falls: A popular spot where the Swift River broadens into a series of smooth slides and pools. On a warm day, you might see brave souls dipping their toes in the icy water.
- Rocky Gorge & Lovequist Loop: Another beautiful area where the river forces its way through a narrow gorge. The easy, flat Lovequist Loop trail on the other side of the bridge offers serene views of the gorge and Falls Pond.
- Loon Mountain Overlook: As you approach the Lincoln side, this pull-off provides a magnificent view of the Pennigewasset Valley and the multi-hued slopes of Loon Mountain.
Afternoon: Emerge in Lincoln. If you have energy, consider a gondola ride at Loon Mountain for an eagle’s-eye view of the color you just drove through.
Dinner & Lodging: Stay in the Lincoln/Woodstock area. The Woodstock Inn Brewery is a fantastic spot for craft beer and a robust meal after a day of exploration.

Day 4: White Mountains to Stowe, Vermont via Route 100

Drive Time: ~3 hours (not including stops)

We bid farewell to New Hampshire and cross into Vermont, the state that arguably defines the classic New England fall aesthetic.

Morning: Take a final, spectacular mountain drive. Consider a detour up the Mount Washington Auto Road (if it’s still open; it typically closes by mid-October depending on weather). Driving your own car to the 6,288-foot summit of the Northeast’s highest peak is an unforgettable experience, taking you through multiple climate zones. Alternatively, for a more relaxed ascent, book a trip on the Mount Washington Cog Railway.
Afternoon: Cross into Vermont and pick up Route 100. This road is Vermont’s spine and is consistently voted one of the best foliage drives in the country. It winds through pastoral landscapes, past classic red barns, white-steepled churches, and covered bridges, all set against a backdrop of fiery mountains.
Must-Stop: Jenne Farm. A short detour off Route 100 near Reading will lead you to what is possibly the most photographed farm in New England. The view of the farmstead nestled in a gentle valley is the quintessential Vermont fall scene. Please be respectful, as it is private property; view from the designated roadside pull-off.
Evening: Arrive in Stowe, a picture-perfect village nestled below the majestic Mt. Mansfield. Check into a classic Vermont country inn, like the Green Mountain Inn on Main Street.
Dinner: Enjoy the vibrant food scene in Stowe. Plate or Harrison’s offer excellent, locally-sourced meals.

Day 5: The Stowe Loop & Craft Discoveries

Drive Time: ~2 hours for the loop

Today is for exploring the Stowe area in depth, a region that offers a perfect blend of natural beauty and refined taste.

Morning: Drive the Stowe Recreation Path. Even if you don’t bike it, driving alongside this paved path provides gorgeous views of the West Branch River, forests, and Mt. Mansfield. Stop for photos at the iconic Stowe Community Church with its white steeple set against the mountain.
Late Morning: Take the auto toll road up Mt. Mansfield (Vermont’s highest peak) or the gondola at Stowe Mountain Resort for a 360-degree view of the foliage sea. The perspective from above is humbling and magnificent.
Afternoon: Vermont is synonymous with artisanal food and drink. Embark on a tasting tour:
- Cold Hollow Cider Mill: Sample fresh-pressed cider and watch donuts being made.
- Ben & Jerry’s Factory Tour: A fun, iconic stop (book ahead).
- Craft Breweries: Stowe is a craft beer haven. Visit The Alchemist (home of the legendary Heady Topper), Von Trapp Brewing Bierhall, or Idletyme Brewing Co.
Evening: Relax and enjoy the small-town atmosphere of Stowe.

Day 6: Stowe to the Berkshires (Stockbridge, MA)

Drive Time: ~4 hours

We journey south into Massachusetts, where the rugged mountains give way to the softer, rolling hills of the Berkshires, a region renowned for its culture and refined beauty.

Morning: Enjoy a leisurely breakfast before heading south. You can take I-89 for efficiency or continue meandering on smaller state routes.
Afternoon: As you enter the Berkshires, the landscape transforms. The colors here often have a different quality—softer golds and russets. Your destination is Stockbridge, a town preserved almost perfectly in time, famously depicted in the paintings of Norman Rockwell.
Mid-Afternoon Stop: Visit the Norman Rockwell Museum. Seeing his original “Four Freedoms” paintings and the countless Saturday Evening Post covers that idealized small-town American life, while you are in the very town that inspired him, is a profoundly moving experience. It adds a layer of cultural and historical context to your scenic journey.
Evening: Check into a historic inn like The Red Lion Inn, which has been operating since 1773. Have a drink on its sprawling front porch and watch the world go by. Dinner at the inn or a nearby restaurant caps off the day.

Day 7: Berkshire Wanderings & Literary History

Drive Time: ~1.5 hours of scenic driving

Dedicate this day to exploring the cultural riches of the Berkshires.

Morning: Drive to Lenox and visit The Mount, Edith Wharton’s stunning estate. Touring the home and walking the formal gardens provides a glimpse into the Gilded Age and offers beautiful views of the surrounding fall landscape.
Afternoon Foliage Drive: Take a drive up Mount Greylock, Massachusetts’ highest peak. The Skyline Drive to the summit rewards you with views that allegedly inspired Herman Melville and Henry David Thoreau. The war memorial at the top stands stark against a panoramic canvas of colorful hills.
Alternative: If you prefer a more active afternoon, hike a section of the Appalachian Trail that traverses the mountain ridge.
Dinner: Lenox and Stockbridge have numerous excellent dining options, from casual cafes to fine dining establishments.

Day 8: Berkshires to Litchfield Hills, CT

Drive Time: ~1.5 hours

We continue south into Connecticut, entering the charming and often-overlooked Litchfield Hills.

Morning: Enjoy a final Berkshire breakfast before a short drive into northwestern Connecticut. This region feels like a well-kept secret, with its own collection of quaint villages and bucolic landscapes.
Afternoon: Your base is Litchfield or a nearby town like Washington. Litchfield’s historic district, with its elegant colonial and federal-style homes, is a delight to stroll through. Drive along backroads like Route 7 and Route 112, which wind past serene lakes, antique shops, and farms.
Must-Do: Drive or Hike at Mohawk State Forest. For one of the best views in the state, drive to the summit of Mohawk Mountain. The lookout tower provides a 360-degree view of the rolling, colorful hills of Connecticut, New York, and Massachusetts. It’s a quieter, more intimate foliage experience than the White Mountains, but no less beautiful.
Evening: Check into a cozy B&B. The Litchfield area is known for its sophisticated yet relaxed dining scene.

Day 9: Coastal Connecticut & The Journey’s End

Drive Time: ~2.5 hours to the coast

For our final act, we trade the inland hills for the dramatic coastline of Long Island Sound.

Morning: Drive south towards the coast. Your destination is the Mystic Country region.
Afternoon: Explore Mystic Seaport Museum, the nation’s leading maritime museum. It’s a recreated 19th-century coastal village, and the historic ships, with their tall masts set against the blue water and the fiery red trees along the shoreline, create a uniquely New England scene. Alternatively, wander through the charming downtown of Olde Mistick Village.
Late Afternoon: Take a final, beautiful drive along Route 1 or Route 146, which hug the coastline, offering glimpses of grand seaside homes, rocky inlets, and marshes glowing with golden grasses and red-hued salt bushes.
Farewell Dinner: Enjoy a spectacular final meal of fresh seafood at a restaurant on the water, such as the Shipwright’s Daughter in Mystic or Abbott’s Lobster in the Rough in Noank. Reflect on the journey from the rocky coast of Maine to this serene southern shore.

Day 10: Departure from Hartford (BDL) or Providence (PVD)

Enjoy a final New England breakfast before a short drive to Bradley International Airport (BDL) near Hartford, CT, or T.F. Green Airport (PVD) near Providence, RI, to drop off your rental car and begin your journey home, your camera roll full and your spirit refreshed by the unparalleled beauty of a New England autumn.

Beyond the Drive: Pro Tips for the Ultimate Foliage Experience

Pack in Layers: New England fall weather is notoriously fickle. Mornings can be frosty, afternoons can be t-shirt warm, and evenings are chilly. Pack a base layer, a fleece or sweater, a waterproof/windproof jacket, and comfortable jeans or hiking pants.
Footwear is Key: You will be walking. A lot. Comfortable, waterproof walking shoes or hiking boots are non-negotiable.
Get Off the Highway: The Interstates are efficient, but the magic is on the state routes and backroads. Don’t be afraid to get “lost.” Some of the best discoveries are down a random dirt road marked “Scenic Byway.”
Respect the Locals & the Land: This is not a theme park; it’s people’s home. Drive carefully, be patient in traffic, don’t block driveways when pulling over for photos, and always respect private property.
Support Local: Skip the chain restaurants and stores. Eat at the family-owned diner, buy syrup from the farm stand, and purchase crafts from the local artisan. It enriches your experience and supports the communities that make this region so special.

Frequently Asked Questions (FAQ)

Q1: What is the absolute best time to see peak foliage on this trip?
This is the million-dollar question. The peak moves southward over a 4-6 week period. For this specific itinerary, which starts in northern New England and ends in the south, the ideal window is typically from September 25th to October 15th. The last week of September will have better color in New Hampshire and Vermont, while the second week of October will be better in Massachusetts and Connecticut. Using the online foliage trackers is essential for fine-tuning your timing.

Q2: How far in advance should I book hotels and rental cars?
As far in advance as possible. For a fall foliage trip, 6 to 12 months is not too early for highly sought-after inns and B&Bs. Rental cars should also be booked several months ahead, as inventory can dwindle and prices surge.

Q3: Is this trip suitable for families with young children?
Absolutely! The key is to build in breaks and choose child-friendly activities. The Conway Scenic Railroad, Ben & Jerry’s factory, Mystic Seaport, and short, easy hikes like Sabbaday Falls are all fantastic for kids. Just be prepared for more time in the car and plan accordingly with snacks and entertainment.

Q4: What are the crowds like? Should I expect traffic?
Yes, you should expect crowds and traffic, especially on weekends on popular routes like the Kancamagus Highway and around Stowe. To avoid the worst of it, try to do your main scenic drives on weekdays, start your days early, and be patient. The beauty is worth the wait.

Q5: I’m a photographer. Any specific tips?
Beyond the standard advice (tripod, polarizing filter, shoot in RAW):

Golden Hour is King: The low-angled light just after sunrise and before sunset makes the colors absolutely sing.
Look for Water: Reflections of colorful trees in lakes, ponds, and rivers double the impact.
Don’t Just Shoot Wide: Zoom in on details—a single red leaf on moss, the texture of bark, a covered bridge framed by color.
Include a Sense of Place: A red barn, a white church steeple, or a classic New England home in your shot adds context and story.

Q6: What if I have less than 10 days?
You can condense the trip by focusing on one or two regions. A superb 5-7 day trip could focus solely on New Hampshire and Vermont (Days 2-5 of this itinerary), which offers the most intense mountain foliage experience.

Q7: Are there any hidden costs I should be aware of?
Be mindful of tolls on the Interstate highways (an E-ZPass transponder is convenient), parking fees in popular towns, and admission costs for attractions, gondolas, and toll roads (like the Mt. Washington Auto Road). These can add up, so budget for them.