Fall Foliage: Our Colourful Leaf-Peeping Road Trip in New England
Planning a hiking road trip during the vibrant autumn months can be an exhilarating experience.
Yet, as project & product managers, we know that even the best-laid plans can change.
Not to mention, it's even harder to find an accommodation within your budget.
Be ready to spend a little more on the lodging to stay in a centralized location with multiple options for restaurants and shops.
Where We Stayed
Let's start with Portland, ME.
Where we stayed at: Courtyard by Marriott Portland Airport
Relatively speaking, it was the most affordable option within a 10-minute drive to downtown Portland.
We only stayed here for a night, but it was a very comfortable airport hotel located near the major highways and a Wal-Mart, should you want to load up on groceries before your road trip.
Now onto Bar Habor, ME.
Where we stayed at: Hanscom's Motel & Cottages
It's by-far the coziest option in Bar Habor, so don't let the 'motel' label fool it.
With a king-size bed, a fully equipped kitchen, and a coastal ambiance, that's just the tip of the iceberg.
Outside, Hanscom's has a community space where you can sip on hot chocolate and share stories around the fire pit.
Next up, Johnsbury, VT.
Where we stayed at: Comfort Inn & Suites Near Burke Mountain
We stayed here the longest and felt like our home away from home.
Their complimentary breakfast and coffee fueled us every morning before our drive & hikes.
The rooms were large to fit 2 queen beds and a sofa bed, which made it easier for us to organize our hiking gear & luggages.
This hotel was within an hour drive to some of the most beautiful fall foliage hikes in New Hampshire.
On deck, Adams, MA.
Where we stayed at: The Trail in Adams
By far, it's the best accomodation to stay at in Adams.
It's not a traditional hotel, instead it's a multi-unit bed-and-breakfast building.
Each room has a theme, for instance we stayed at the 'Greek Room' with a blue-hue and matching decors.
We had planned to stay an additional night for a room with a sauna, but we decided to drive & spend the weekend in Boston instead.
Closing the loop in Downtown Boston, MA.
Where we stayed at: The Dagny Boston
Formerly the home of the Hilton Boston, this luxury boutique hotel is located in the heart of downtown with a highly-rated coffee shop and oyster restaurant.
Once we valeted our rental car, we simply walked around the harbor, Boston Commons, and especially the Sam Adams taproom.
You can even reach the delicious Italian restaurants in the North End in under 20 minutes on foot.
Though, be aware that valet parking costs over $60 USD per 24 hour period.
Where We Hiked
Ocean Path Trail (at Acadia National Park)
The Ocean Path Trail in Acadia National Park offers a stunning coastal adventure that you won't want to miss.
This moderately easy 2.2-mile trail runs along the rocky coastline, treating hikers to breathtaking ocean views and the soothing sound of crashing waves. The terrain is relatively flat, making it accessible for hikers of various skill levels.
While hiking poles aren't a necessity, they can provide extra stability, especially if you want to explore some of the rocky offshoots. You should definitely try this trail if you're looking for a serene coastal experience with endless photo opportunities.
Franconia Notch Path (at Franconia Notch State Park)
The Franconia Notch Path is a picturesque trail that takes you through Franconia Notch State Park in New Hampshire.
This 4.3-mile path offers a mix of forested areas and open meadows with beautiful mountain views. The terrain is relatively mild, so hiking poles aren't required, but they can be helpful if you prefer added support.
This trail is perfect for those who want to experience the natural beauty of the White Mountains without tackling a strenuous hike. It's a great introduction to the region's breathtaking landscapes.
Mount Willard Trail (at White Mountain National Forest)
Mount Willard Trail in the White Mountain National Forest is a 3.2-mile hike that leads to a stunning lookout point.
The terrain varies from well-maintained paths to some steeper sections. While hiking poles aren't mandatory, they can provide extra stability on the steeper parts. This trail is a must-try for those seeking a rewarding view with a moderate level of effort.
The vista at the top overlooks Crawford Notch and is especially enchanting in the fall when the foliage bursts into vibrant colors.
Bald Mountain (at Franconia Notch State Park)
Bald Mountain in Franconia Notch State Park is a 1.5-mile trail that takes hikers through a lovely forested area.
The trail is moderately steep in sections, but hiking poles are not necessary. The real beauty of this hike is the incredible panoramic view you'll find at the summit, which is a fantastic reward for a relatively short and straightforward hike.
This trail is perfect for those who want a quick outdoor escape and a postcard-worthy view.
Artist Bluff Trail (at Franconia Notch State Park)
The Artist Bluff Trail is a short but sweet 1.5-mile hike that offers stunning views of Echo Lake and Cannon Mountain. The terrain is relatively mild, and hiking poles are not required.
This trail is a must-try for those who love fantastic vistas without an all-day commitment. It's also great for families and amateur photographers looking for that perfect shot.
North Sugarloaf Trail (at White Mountain National Forest)
North Sugarloaf Trail is a 3.6-mile hike through White Mountain National Forest.
The terrain is moderate, with a gradual ascent to the summit. While you don't need hiking poles, they can be handy for stability on some rocky sections.
This trail is ideal for those seeking a moderately challenging hike with stunning views of the surrounding landscape. The panorama at the top of North Sugarloaf is well worth the effort.
Middle Sugarloaf Trail (at White Mountain National Forest)
Middle Sugarloaf Trail is a 2.8-mile hike in the White Mountain National Forest. The terrain can be rocky in places, so hiking poles can be helpful for balance.
This trail is perfect for those who enjoy a moderate hike leading to a fantastic viewpoint. The summit provides a memorable vantage point overlooking the stunning White Mountains.
Mount Greylock Overlook Trail (at Mount Greylock State Reservation)
The Mount Greylock Overlook Trail in Massachusetts is a 2.8-mile path known for its serene forest setting and views of Mount Greylock.
While the trail itself is relatively gentle, some rocky sections can benefit from hiking poles for added stability. This trail is perfect for those wanting a tranquil hike in the woods, culminating in a beautiful view of the surrounding landscape.
Ashuwilticook Rail Trail (in Berkshire, Massachusetts)
The Ashuwillticook Rail Trail in the Berkshires offers a 12.7-mile paved route for hikers, bikers, and runners.
The terrain is flat, so hiking poles are not necessary. This trail is fantastic for families, leisurely cyclists, or those who want a relaxing walk with beautiful water views. It's an excellent choice for a low-impact outdoor excursion.
Boston's Freedom Trail (starting at Boston Common)
Boston's Freedom Trail is a 2.5-mile historical walk through the heart of Boston, highlighting important landmarks from American history.
Practical Takeaways
Book early, even in off-season. Fall is prime foliage time in New England — hotels near Acadia and the White Mountains fill up quickly. Aim to reserve at least 2–3 months ahead.
Stay central, not cheapest. You’ll save time (and stress) by choosing accommodations within a 10–15-minute drive to downtowns or trailheads. Paying slightly more for location pays off in spontaneity.
Mix hotel types. Alternate between chain hotels (for reliability and breakfast) and local motels or B&Bs (for charm and character). The variety keeps the trip interesting and budget balanced.
Keep flexible weather gear. Autumn weather changes fast — bring waterproof layers and an extra fleece. Morning fog can roll in quickly on coastal trails.
Start early on trail days. Parking lots at Acadia and Franconia Notch fill up by mid-morning. Early starts also mean better light for photography and fewer crowds.
Reward yourself. Each town has a hidden gem — Bar Harbor’s cozy cafés, St. Johnsbury’s local diners, and Boston’s North End trattorias. Don’t rush the drives; savor the small stops.
Final Thoughts
Our New England fall road trip stretched over 1,000 kilometers over seven days, winding through four states.
From Maine’s rugged coastlines to Vermont’s mountain passes and back down to Boston’s brick-lined streets.
Planning this route taught us that the best adventures balance structure with spontaneity.
You can plan the routes, book the rooms, and map the trails — but the magic happens in the in-betweens:
The fog lifting off the Atlantic.
The crunch of leaves underfoot.
If you’re thinking about a fall road trip, just do it.
Start small, stay flexible, and let the map lead you somewhere unforgettable.
