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Have you been dreaming of witch trials sites, fiery maple trees, and scenic rural drives? For fall lovers, one week exploring the vibrant foliage of New England is the ultimate bucket list experience. An adorer of autumn myself, I wrote the perfect 7 day New England road trip itinerary to fulfill your leaf peeping dreams.
This itinerary is inspired by my own road trip through New England last year, which included New Hampshire, Vermont, and Massachusetts. Although my home state of Ohio has gorgeous falls too and I’d already seen Massachusetts at peak coziness, I yearned to more deeply explore the hilly forests and farmland of the Northeastern United States. Sneaking in a lobster roll or two while revisiting Massachusetts wouldn’t hurt either!
New England’s compactness makes it easy navigate, while offering charming small towns, rewarding hiking trails, and coastal views. As this road trip covers three states, I’ve carefully planned this itinerary for the most efficient New England sightseeing route. Are you ready to get witchy in Salem, MA and cozy in Woodstock, VT? Let’s get into it.
Ultimate 7 Day New England Road Trip Itinerary
I have mapped out the below itinerary to further ease your navigation between these amazing New England destinations.
Related: 61 Awesome Bucket List Ideas for Your Best Fall Ever
Day 1: Massachusetts – Arrive Into Boston
This 7 day New England road trip itinerary kicks off in Boston, whose urban streets transform under autumn’s spell, particularly in the Beacon Hill neighborhood. If you are flying, you’ll land at Boston Logan International Airport, so grab a 10-minute Uber/Lyft into the city. Arriving either in the morning or the night before allows you to have a full day of sightseeing what they call “Beantown”.
The best thing to do during one day in Boston is to follow the Freedom Trail past sites significant to Boston’s Revolutionary War history. Either join a guided tour or simply follow the red line on the pavement from Boston Common. This self-guided app also provides an informative tour at your own pace.
Afterwards, stroll the boutiques and cobblestone streets of Beacon Hill or consume seasonal treats on the Underground Donut Tour.
Finish by dining at one of many Italian restaurants in Boston’s North End before turning in for the night. Don’t forget to stop in for a cannoli at Modern Pastry or a Boston cream donut at Bova.
Craving a spooky experience, but tired of walking? Take this Boston Ghosts and Gravestones Trolley Tour.
Suggested Stay: Courtyard by Marriott Boston Downtown/North Station
Day 2: Massachusetts – Salem, MA
No single 7 day New England itinerary would be complete without a visit to the Witch City, or Salem, MA, where the infamous 1692 witch trials took place. To make the 45-minute drive from Boston, pick up your rental car the morning of day two (we rented ours at the airport).
Note: If visiting during the super busy month of October, get into Salem by 9am to ensure you find parking and avoid traffic jams. An alternative is to stay in Boston for one more night and take a 30-minute train or ferry into Salem. I recommend booking a room at Courtyard by Marriott Boston Downtown/North Station to be close to both the train and Freedom Trail.
Here is the best way to spend one day (also consider following my Salem day trip itinerary):
- Visit the Salem Witch Museum (purchase a timed entry ticket online)
- Stop into the Salem Witch House
- Stroll past the wand shops, fortune tellers, and apothecaries of Essex Street
- Take a spooky witch trials walking tour
For a nice dinner with lots of ambiance, dine at Ledger Restaurant. For less fuss and laid-back vibes, get a lobster roll and beer at The Lobster Shanty; they serve delicious clam chowder too!
Suggested Stay: In Salem at the Hampton Inn Salem Boston or in Boston at the Courtyard by Marriott Boston Downtown/North Station
Related: 13 Best Things To Do In Salem, MA In October
Day 3: New Hampshire – Artist Bluff Trail
It’s time to get out of the city and into the White Mountains of New Hampshire, which deliver sweeping views over fall’s colorful tree canopies. On the morning of day three, depart from Massachusetts and drive about two hours north to Lincoln, New Hampshire. While there are plenty of hotels in and around Lincoln, you may opt to stay in a cozy cabin instead.
Recommended Hotel: Holiday Inn Express & Suites Lincoln East – White Mountains
You can find cabins all around the area, so I recommend doing a search on Airbnb and seeing what’s available during your travel dates. My husband and I stayed in this adorable dog friendly cabin in Wentworth, New Hampshire last year, where the stargazing looked like a sheet of glitter over the sky.
After settling in, it’s time for your first hike of the trip: the 1.5-mile Artist Bluff Trail in Franconia State Park. This steep loop trail leads to panoramic views over the fiery-colored treetops framing Echo Lake. For less climbing, take the Cannon Mountain Aerial Tramway just one mile away, which lifts you 4,080 feet to the peak of Cannon Mountain.
If you still have time and energy, also consider hiking the gorgeous two-mile Flume Gorge loop trail, which follows along an 800-foot natural gorge at the base of Mount Liberty. Just remember this trail has an entry fee of $18 online (book here) and $21 at the trailhead.
After hiking, visit a local brewery, like Rek-Lis Brewing Company, for dinner and drinks. As we were staying closer to Plymouth, NH, we stopped into Sole Track Brewing to share a tasting paddle. For dinner, we grabbed burgers at The Last Chair, a ski-themed brewery that had tasty burgers and peanut butter porter.
Day 4: New Hampshire – Kancamagus Highway
The next day in New Hampshire, you will experience the state’s most iconic leaf peeping adventure: the Kancamagus Highway. This 34.5-mile stretch of roadway between the towns of Lincoln and Conway leads past beautiful mountainscapes and other gorgeous natural scenery.
Keep in mind there are no gas stations along this route, so fill up before heading out. Also, you must pay $5 per day to park in White Mountain National Forest. You can simply put the cash or check in an envelope to leave at a drop box at the first stop along the highway.
Don’t be afraid to pull over frequently along the Kancamagus Highway. Otherwise, this enchanting stretch only takes about one hour to complete without stops.
Here are the must-see sights along the Kancamagus Highway, in order heading east:
- Otter Rocks
- Hancock Overlook
- Panoramic Overlooks
- Pemigewasset Overlook
- CL Graham Wangan Overlook
- Sugar Hill Scenic Vista
- Sabbaday Falls: Most popular hike along the way, only .5 mile trail that leads to a waterfall
- Russell-Colbath House
- Campney Fall: 3.1 miles out and back, .6 miles additional miles to reach the summit of Mount Chocorua, which has gorgeous 360-degree views
- Rocky Gorge: lovely in fall and nice place to picnic
- Lower Falls: this super short hike to a waterfall is the most popular stop of the drive
- Albany Covered Bridge
Stay overnight near Lincoln, NH again. If you are staying in a cabin, consider having a cookout or bonfire to make s’mores!
Otherwise, dine out at Moat Mountain Smokehouse and Brewery in North Conway before turning back to drive the Kancamagus Highway in reverse. You could also visit Woodstock Inn Brewery in North Woodstock upon completion of the drive.
Day 5: Vermont – Woodstock
The next morning, it’s time for the last leg of your trip: the friendly small towns of Vermont where even the automated speed signs scold you politely.
The drive to charming Woodstock (the one in Vermont, not New Hampshire) will only take about and hour and a half from Lincoln, NH. You could stay in a hotel in Woodstock or simply book an Airbnb in the surrounding area (we loved this adorable hobby farm).
Recommended Hotel: The Village Inn of Woodstock
This route around Woodstock will be the delight of any 7 day New England road trip itinerary:
- Quechee Gorge: Visible from an overpass along Route 4, this 165-feet gorge (Vermont’s deepest) was formed by glaciers 13,000 year ago. You can park in a lot off Route 4 to quickly view the gorge or hike the Quechee Gorge Trail at Quechee State Park.
- The Skinny Pancake: A great breakfast/brunch stop in Quechee. I loved my savory crepe with apple, brie cheese, and a locally sourced blueberry compote.
- Woodstock: Explore the antique shops, cafes, and lovely covered bridges of this charming small town. Don’t forget that all parking is paid – even along the street!
- Billings Farm and Museum: For $17 you can explore the grounds and stables of this working farm tucked among the rolling hills. I purchased a small apple cider to sip as I strolled past dairy calls being milked, goats perched on top of fences, and horses grazing. Check their calendar for daily events.
- Woodstock Farmers Market: The perfect stop for locally produced products, like cheese and maple syrup.
- President Calvin Coolidge Historic Site: The site of several preserved buildings from Calvin Coolidge’s childhood home at Plymouth Notch, including his family homestead. Also see where the 30th president of the United States attended church, his father’s store, the post office, and Coolidge’s summer white house office inside of a dance hall.
Make a reservation to dine in downtown Woodstock at The Prince & The Pauper Restaurant or Santé.
Travel Savvy Tip
With the rise of social media, certain farms around the Woodstock area have become popular photo spots for Instagrammers. Sadly, this has escalated into a problem for local residents, with visitors clogging roads and trespassing onto private property.
Local governments have begun taking action, closing roads leading to Jenne Farm and Sleepy Hollow Farm during the month of October. Please respect these rules – there are plenty of other gorgeous locations all around Vermont to photograph!
Day 6: Vermont – Grafton
To get a true small town Vermont experience, drive one hour south of Woodstock to the tidy little village of Grafton. Grafton is especially pleasing during peak foliage season, when bright shades of red, orange, and yellow frame tall white church steeples and local shops.
However, don’t confuse Grafton’s impressive collection of well-preserved historic buildings for an open-air museum. This is a functioning, tight-knit community that still holds Gilmore-Girls-style town meetings to this day.
Just be sure to download any maps before heading out, as I found the town’s cell service to be weak to nonexistent.
Here are the best points of interest to check out in Grafton’s quaint and walkable town center:
- Learn about making maple syrup at Plummer’s Sugar House before buying some to take home with you.
- Hike a trail at the Grafton Trails & Outdoor Center. Grafton also has a cute welcome sign a bit further south down Grafton Road.
- Journey to the past at the Grafton Historical Society.
- Sample local cheese varieties at the Grafton Village Cheese Company.
- Browse locally produced gifts and home goods at Mercantile and adjacent Dover House Antiques.
- Wander into the Turner Hill Interpretive Center to learn the story of Alec Turner, who settled in Grafton and to raise his family after escaping slavery.
- Check out the Nature Museum to learn about native New England flora and fauna and wander down various nature trails.
- Discover unique copper sculptures honoring Northeastern Native Americans at Jud Hartman Gallery.
If you get hungry, the Grafton Village Store has you covered for coffee, pastries, and simple meals. For a sit-down dinner, book a reservation at the rustic Phelps Barn Pub or the cozier 1801 Tavern at The Grafton Inn.
Day 7: Complete Your New England Road Trip Itinerary at Boston Logan Airport
Just as the leaves must eventually fall to the ground, this New England road trip itinerary must reach its end too. Hopefully you had the fall foliage experience you’ve been dreaming about and are already planning your return trip!
If you drove from your house, then it’s time to make the trek back home. Otherwise, the drive from Woodstock, Vermont to Boston Logon International Airport will take about two and a half hours. I recommend arriving two to three hours before your flight to have time to drop off your rental car, check any bags, and find your gate.
Is Your New England Road Trip Itinerary Longer Than 7 Days?
There are so many options for New England itinerary add-on’s:
- Consider spending one extra day in Boston.
- Stay in Salem, MA for two days and day trip to nearby Danvers (formerly Salem Village) to see even more witch trials sites!
- Explore additional charming towns along the Vermont and New Hampshire border, including White River Junction, Windsor, Hanover, and Battlebro.
- Add an extra day to New Hampshire to take advantage of countless more hiking trails.
- Add an additional state: Maine! Explore trendy Portland, eat lobster rolls in Bar Harbor, or go hiking at Acadia National Park.
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There you have it – the recipe for a dreamy and memorable 7 day road trip itinerary through New England. It’s the best combination of the bustling Atlantic coast of Massachusetts, the mountains of New Hampshire, and the farms of Vermont. You’ll see exactly why New England is beloved by leaf peepers, maple syrup addicts, and outdoor lovers alike!
What dates were you in New England? I’m going to be in Woodstock late Sept (26-28) and hoping to see some good color….
This was around that same time – late September. As far as color, that timeframe is likely to be a little on the early side. First to second weekend of October is more ideal. That said, the leaves were starting to change during our visit.