If there’s one thing New England knows how to do right, it’s Fall. And what better way to experience it than with a good old-fashioned road trip? In this post, I’m sharing the ultimate 7 day New England Fall road trip itinerary from Boston, including six New England destinations you won’t want to miss! Plus, I’ve got you covered with all the best things to do in New England in Fall, restaurants to check out, where to stay, and more!

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Ultimate New England road trip itinerary in Fall
Ready to hit the road and embark on a Fall-tastic East Coast road trip through New England? Picture winding roads lined with a kaleidoscope of colors, quaint villages boasting the coziest coffee shops, and all the apple cider donuts and pumpkin-spiced lattes your heart desires. That’s Fall in New England in a nutshell, and I’m still dreaming about it!
Last year, we had the opportunity to spend a whole week in New England in the Fall, which was truly a magical experience I’ll never forget! However, this was also our first leaf-peeping adventure in New England, and although I did a ton of research in advance, anything that could go wrong did, and there are so many things I wish I had known prior to our trip to make it even more enjoyable.
But fear not, in this post, I’m sharing the ultimate road trip itinerary New England, packed with all the best places to visit in New England, must-see stops on the Kanc, tips for visiting New England Fall, hidden gems you don’t want to miss, and so much more! Happy Fall Y’all!
Planning in a hurry? Check out these quick links!
Travel resources:
- Skyscanner (find the best rates on airplane tickets)
- Discover Cars (compare rental car prices and save $$$)
- Booking.com (find the best deals on accommodations)
- Portsmouth >> Hotel Thaxter
- Portland >> Cambria Hotel Portland Downtown Old Port
- Conway >> Kearsarge Inn
- Woodstock >> Woodstock Inn & Resort
- Stowe >> Trapp Family Lodge
- Salem >> Hawthorne Hotel
DISCLOSURE: This post contains affiliate links, so we may earn a small commission when you make a purchase through links on our site at no additional cost to you.
New England road trip itinerary
Things to know before you go

Where is New England?
New England is a region in the northeastern United States, consisting of six New England states: Maine, New Hampshire, Vermont, Massachusetts, Rhode Island, and Connecticut. It’s known for its rich history, picturesque landscapes, and vibrant fall foliage, making it a popular destination for travelers seeking scenic beauty and charming small towns.
Map of New England
New England weather in Fall
The weather in New England varies throughout the region, but generally, temperatures start to gradually drop from the mild highs of summer to cooler, more comfortable levels in early Fall. September can still feel quite warm, with average daytime temperatures ranging from the 60s to the low 70s, while nights may start to become cooler, dipping into the 40s and 50s.
As October arrives, temperatures continue to decrease, and it can get quite chilly. Daytime temperatures typically range from the 50s to 60s, with nights getting colder, often dropping into the 30s and 40s. October also tends to be the wettest month of the season (I know this from personal experience), with intermittent showers and overcast days, but don’t let it get you down. You can’t control the weather!
Tips for visiting New England in Fall
- Fall is a popular time to visit New England, especially during peak foliage in October, so make sure to plan ahead and book accommodations well in advance. We started looking in July (a few months before), and most hotels were already sold out or extremely expensive. Consider staying in charming bed and breakfasts, cozy cabins, or historic inns for an authentic New England experience.
- Timing is key when it comes to experiencing peak Fall foliage in New England. While the season typically spans from late September to late October, the timing can vary depending on factors like elevation and weather conditions. Keep an eye on foliage reports and consider visiting different parts of New England to catch the best time to visit New England for Fall colors.
- While it’s important to map out your itinerary ahead of time, remember to be flexible. Research scenic drives and attractions along your route, but also be prepared to adapt. Cell service can be spotty, especially along the Kancamagus Highway, so it’s essential to have a general idea of your route before you depart. And if you’re ever in doubt, just follow the tour buses (haha)!
- Although sleeping in on vacation is always nice, aim to start early. I can’t even tell you how many tour buses I saw roll in as early as 10 am! If possible, I also recommend visiting popular attractions and scenic drives during weekdays to avoid large crowds and traffic.
- While it’s important to have somewhat of a plan in place, be flexible with your itinerary, take the scenic route, and allow yourself to get lost in the charm of small-town New England. Some of the best memories are made when you least expect them, so keep an open mind and be willing to go with the flow.
- Don’t forget to stock up on snacks, water, and other road trip essentials to keep you fueled and hydrated throughout your New England Fall foliage road trip. To be safe, I would also consider packing a roadside emergency kit with items such as a flashlight, first aid supplies, and a portable phone charger. Click here to browse my road trip packing list on my Amazon storefront.
Looking for more New England road trip tips? Check out this post >> Road trip ready: Best New England Fall road trip essentials
What to pack for New England
- Layers are key. Fall weather in New England can be unpredictable, with chilly mornings, mild afternoons, and crisp evenings. Be sure to pack plenty of layers, including sweaters, long-sleeve shirts, and lightweight jackets, to stay comfortable throughout the day. Don’t forget a waterproof jacket or windbreaker to shield you from any unexpected rain showers or gusty winds.
- Comfortable footwear. With so much to explore, comfortable footwear is a must for any fall adventure in New England. Whether you’re hiking scenic trails, wandering through charming towns, or strolling along rocky coastlines, opt for sturdy shoes or boots with good traction to keep your feet happy and dry. Don’t forget to pack a pair of cozy socks for those cooler evenings by the fire.
- Fall accessories. No fall wardrobe is complete without some essential accessories to keep you warm and stylish. Be sure to pack a cozy scarf, gloves, and a knit hat to ward off the chill on brisk days. A versatile scarf can also double as a makeshift blanket for cooler days. And don’t forget sunglasses to protect your eyes from the bright autumn sun.
- Daypack or tote bag. A lightweight daypack or tote bag is essential for carrying all your essentials while exploring New England. Pack a water bottle, snacks, camera, and any other necessities you may need for a day of adventure. Look for a pack with comfortable straps and multiple compartments to keep your belongings organized and easily accessible. Click here to check out my all-time favorite backpack for any trip.
- Camera or Smartphone. Fall in New England is a photographer’s dream, with stunning landscapes, vibrant foliage, and charming towns begging to be captured on camera. Be sure to pack your camera or smartphone to document your adventures and create lasting memories of your fall getaway. Don’t forget extra memory cards or a portable charger to ensure you never miss a shot.
- Fall outfits. Embrace the cozy vibes of fall with a wardrobe inspired by the season’s colors and textures. Pack flannel shirts, plaid scarves, denim jeans, and neutral sweaters to blend in seamlessly with the autumn landscape. And don’t forget to leave some room in your suitcase for souvenirs, like locally made crafts or artisanal goods, to bring a piece of New England home with you.
Need some help packing for your Fall New England road trip? Check out this post >> How to create the ultimate Fall travel capsule wardrobe

7 day New England road trip itinerary
- Day 1 (1 night): Portsmouth, New Hampshire
- Days 2-3 (2 nights): Portland, Maine
- Day 4 (1 night): North Conway, New Hampshire
- Day 5 (1 night): Woodstock, Vermont
- Day 6 (1 night): Stowe, Vermont
- Day 7 (1 night) Salem, Massachusetts
Best New England road trip destinations

First stop >> Portsmouth, New Hampshire
DAY 1: Fly into Boston Logan International Airport (BOS)
- Pick up rental car and check into Hotel Thaxter
- Freshen up and head downtown for afternoon/evening
- Grab lunch at Fezziwig’s (Note: They are closed Monday’s & Tuesday’s)
- Spend some time exploring downtown and shopping
- Grab a beer at Earth Eagle Brewings (Optional spot: The Oar House)
- Enjoy happy hour from 3:30 pm-6 pm daily at The Wilder
- Grab a photo of the North Church of Portsmouth at sunset
- Head to dinner at Moxy (Optional spot: Botanica Restaurant & Gin Bar)
- Call it a night early so you’re refreshed for a busy day tomorrow!
Check out this video >> DAY 1 of our 7 day New England road trip itinerary
A few more best hotels in Portsmouth
- Luxury: Wentworth By The Sea (ocean views + on-site restaurants)
- Mid-Range: The Inn Downtown (close to Downtown + spacious rooms)
- Budget: Courtyard by Marriott Portsmouth (free parking + good location)

Second stop >> Portland, Maine
DAY 2: Explore Portsmouth and drive to Portland, Maine
- Grab coffee and breakfast at Cup of Joe Cafe & Bar
- Walk down to Prescott Park (Make sure to grab photos of the gardens)
- Spend a couple of hours at Strawbery Banke (buy tickets here)
- Grab lunch at Popovers on the Square
- Grab photos of the Portsmouth Harbor Lighthouse (from Ocean Street)
- Start the drive to Portland (about an hour drive)
- Check into Cambria Hotel Portland Downtown Old Port
- Freshen up and head to happy hour at Blyth & Burrows
- Go to dinner at Eventide Oyster Co (book a reservation here)
- Grab a nightcap at Lincolns (cash-only speakeasy) and head home
Check out this video >> DAY 2 of our 7 day New England road trip itinerary
A few more best hotels in Portland Maine
- Luxury: The Press Hotel (in Portland Downtown Historic District)
- Mid-Range: Portland Harbor Hotel (near Portland waterfront
- Budget: Hyatt Place Portland-Old Port (free shuttle service)

DAY 3: Spend the day exploring Portland and enjoy a food crawl
- Start your food crawl bright & early at The Holy Donut (be prepared to wait)
- Go on a sightseeing tour of Portland in a vintage fire truck (book here)
- Go to The Highroller for lunch and order the Lobster cheese crisp taco
- Drive over to the Portland Head Light & spend some time walking around
- Drop off car at the hotel and walk over to Shipyard Brewing Company
- Walk over to J’s Oyster for some seafood with a view
- Pop over to Gilberts Chowder House for a bowl of clam chowder
- Stop at Duckfat (last spot on your food crawl) for some Belgian-style frites
- Head back to hotel to relax for the rest of the evening!
Check out this video >> DAY 3 of our New England road trip 7 days
A few more best things to do in Portland Maine
- Sightseeing tour (Explore hidden gems + 3 lighthouses)
- Walking food tour (stops at 7 different eateries)
- Private sunset charter (bring your own food & drinks + amazing views)
- Brewery & spirits tour (stops at three local breweries around Portland)
- Explore Peaks Island (click here for the ferry schedule)
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Check out this related read >> The best places to visit in New England (especially in Fall)

Third stop >> North Conway, New Hampshire
DAY 4: Drive to Conway and spend the day exploring
- Grab breakfast at Coffee ME Up and start the drive to Conway
- Head to Diana’s Baths and hike to waterfalls (only 1.1 hike round-trip)
- Drive to Cathedral Ledge lookout (great photo spot FYI)
- Enjoy a picnic lunch with a view
- Check into The Kearsarge Inn and freshen up
- Drive to Mount Washington Auto Road
- Take your time driving the auto road (15 miles round-trip)
- Make sure to grab a photo with the Mt Washington Summit sign at the top
- Drop off car at hotel and walk to Deacon Street for a martini
- Pop into Zeb’s General Store for some souvenirs
- Grab dinner at Muddy Moose Restaurant & Pub
Check out this video >> DAY 4 of our one week New England road trip itinerary
Our experience on Mount Washington Auto Road
I’m not lying when I say this was probably one of the scariest rides of my life (haha). We were warned before entering that it might be “foggy” at the top, but I apparently didn’t realize what that meant. Picture driving up a steep, winding mountain with no guard rails and barely any visibility. Sounds terrifying, right? If there’s one piece of advice I can give, it’s to go on an absolutely clear day, or it’s honestly a waste of money. Otherwise, I’m sure the views are stunning!
If you’re interested in driving Mount Washington Auto Road, the admission is $45 per car + $20 per passenger, and it is 7.6 miles to the top. The auto road is always weather-permitting and can only be accessed from 9 a.m. to 4 p.m. I recommend taking your time and allowing a couple of hours to drive up and down the mountain, and make sure to stop at some of the scenic pull-offs for photos! Click here for more details.
A few more best things to do in North Conway
- Conway Scenic Railroad (click here to book tickets)
- The Mount Washington Cog Railway (click here to book tickets)
- Bring the kids to Storyland (click here to book tickets)
- Explore Cranmore Mountain Resort

DAY 5: Drive the Kancamagus Highway and head to Woodstock
- Grab coffee and breakfast at Cafe Italia and check out of hotel
- Head to the Kancamagus Highway and take your time driving
- Stop at the Albany Covered Bridge
- Stop at Lower Falls (try to get there early)
- Stop at Sugar Hill Overlook or Hancock Overlook (or both hehe)
- Stop at Lincoln Woods Trailhead (fave spot on The Kanc)
- Continue drive to Woodstock and stop at Woodstock Inn Brewery for lunch
- Stop at Flume Gorge (book your reservation in advance here)
- Stop at Artists Bluff (steep 1.5 miles round-trip + incredible views)
- Optional stop at Echo Lake (entry fee is $4 per person)
- Drive to Woodstock and check into Woodstock Inn & Resort
- Freshen up and head to The Red Rooster in the hotel for dinner
Check out this video >> DAY 5 of our ultimate New England road trip itinerary
Kancamagus Highway Map
Tips for driving the Kancamagus Highway Fall
- Get started early! Beat the crowds and make the most of your day by starting your drive early in the morning. Not only will you avoid traffic (and many tour buses), but you’ll also have the opportunity to witness a stunning sunrise unlike any other. Alternatively, consider staying late to watch the sun set behind the mountains, casting a warm glow over the foliage. Trust me, no filter will be needed!
- Take your time! While the destination is undoubtedly stunning, don’t forget to enjoy the journey itself. The Kancamagus Highway spans 34 miles of pristine wilderness, offering numerous scenic overlooks, hiking trails, and picnic spots along the way. Take your time to stop at these points of interest, breathe in the crisp mountain air, and immerse yourself in the tranquility of nature.
- Pack some road trip essentials. Before embarking on your drive, ensure you’re well-prepared for a day on the road. Pack essentials such as water, snacks, a camera, binoculars for wildlife viewing (if that’s your thing), and a map or GPS device. Cell phone reception can be spotty in certain areas, so I recommend mapping out your stops ahead of time or making sure you have a backup navigation method.
- Make sure you’re fueled up. Although there are gas stations located near the Kancamagus Highway, they are not directly on the highway itself, so it’s advisable to fill up your tank before starting your journey. If you are getting close to empty, the closest towns with gas stations to the Kancamagus Highway include Lincoln, Conway, and North Conway.
Other places to stop on the Kancamagus Highway
- Sabbaday Falls. This picturesque waterfall, located about 3 miles west of the Kancamagus Highway on Sabbaday Falls Trail, is a must-see. Surrounded by vibrant New Hampshire Fall foliage, it offers a tranquil setting for a short hike and some stunning photo opportunities.
- Champney Falls. Nature lovers won’t want to miss Champney Falls, a scenic hike that leads to a breathtaking waterfall surrounded by colorful foliage. The trail offers glimpses of the vibrant hues of fall as you make your way through the forest to the cascading waters below.
- Rocky Gorge Scenic Area. Located off the highway, Rocky Gorge Scenic Area is a popular stop for its stunning views of the Swift River and the rocky gorge below. Take a leisurely walk along the riverbank and soak in the beauty of the New England fall foliage reflected in the crystal-clear waters. Make sure to cross the river via the bridge to check out Falls Pond too!
- Franconia Notch State Park. While slightly off the Kancamagus Highway, Franconia Notch State Park is well worth a visit during the fall season. Explore attractions such as Flume Gorge (book reservation in advance here), Artists Bluff (my favorite Fall road trip New England attraction), Cannon Mountain Aerial Tramway, and Echo Lake Beach, all surrounded by breathtaking fall foliage.
- Pemigewasset Overlook. For sweeping panoramic views of the White Mountains ablaze with fall colors, make a stop at the Pemigewasset Overlook. From this vantage point, you’ll be treated to a breathtaking vista of the surrounding landscape, with hues of red, orange, and gold stretching out as far as the eye can see.

Fourth stop >> Woodstock, Vermont
DAY 6: Spend the day exploring Woodstock and head to Stowe
- Grab breakfast at Mon Vert Cafe (be prepared to wait)
- Spend some time walking around & exploring Downtown Woodstock
- Take photos at Woodstock Middle Covered Bridge
- Pop into Gillingham’s General Store for a souvenir
- Grab photos in front of Woodstock Inn before leaving Woodstock
- Head to Woodstock Farmers Market for lunch
- Drive through the Taftsville Covered Bridge
- Head to Sugarbush Farm & enjoy a maple syrup and cheese tasting
- Drive to Quechee Gorge State Park for some hiking
- Start drive to Stowe and stop at Long Trail Brewing Co on the way
- Check into Trapp Family Lodge
- Have dinner at Von Trapp Brewing Bierhall (book reservation here)
Check out this video >> DAY 6 of our East Coast Fall road trip

Fifth stop >> Stowe, Vermont
DAY 7: Spend the day exploring Stowe and head to Salem
- Grab coffee & breakfast at Black Cap Coffee (be prepared to wait)
- Spend some time walking around & exploring Stowe
- Buy a souvenir at Shaw’s General Store
- Grab a photo of the Stowe mural (Location >> Laughing Moons Chocolates building)
- Head over to the Stowe Gondola Skyride (book in advance here)
- Grab a photo on the way of Stowe Community Church in the distance
- Have lunch at Cliff House at the top of Gondola Skyride (book reservation here)
- Drive Smugglers Notch Scenic Highway
- Start drive to Salem and stop at Cold Hollow Cider Mill on the way
- Check into Hawthorne Hotel & have dinner at The Tavern (book here)
Check out this video >> DAY 7 of our 7 day New England road trip itinerary
A few more best hotels in Stowe
- Luxury: The Lodge at Spruce Peak (ski-in/ski-out resort with spa)
- Mid-range: Field Guide Lodge (free parking + great location)
- Budget: The Little River Inn (close to Downtown + cozy B&B)

Last stop >> Salem, Massachusetts
DAY 8: Spend the day exploring Salem and head home
- Start the day with coffee & breakfast at Jaho Coffee Roaster
- Go on a guided walking tour to explore the area (click here to book)
- Grab photos at Old Town Hall & Ropes Mansion
- Grab lunch at Red’s Sandwich Shop
- Explore the Peabody Essex Museum (grab tickets here)
- Spend some time shopping and don’t forget to buy a souvenir!
- Grab a drink at The Roof for the best views in town
- Start drive back to Boston Airport and fly home
Alternate itinerary >> Go on a Hocus Pocus movie locations tour instead of a general walking tour
Traveling from Boston to Salem? Grab ferry tickets here >> Salem High Speed Ferry to/from Boston
Other things to do in Salem
- Salem Night Ghost Tour (explore the city’s spooky past at night)
- Sailing Tour in Salem Sound (great for families + beautiful views)
- Booze & Brews Haunted Pub Crawl (stops at Salem’s best watering holes)
- Tour the House of Seven Gables (click here to grab tickets)
- Tour the Witch House (snag tickets here)

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