After years of seeing those viral fall foliage photos, I finally planned my own New England road trip and it lived up to the hype.
But planning a huge New England fall road trip to hit peak fall foliage across three states I’d never visited before was not easy. If you love spooky Salem vibes, charming towns, leaf peeping, and pumpkin spice lattes but aren’t sure how to plan your trip, I got you.
Keep reading for my exact road trip itinerary plus tons of tips to help you plan the ultimate New England fall foliage road trip.
Why New England in the Fall Is a Bucket List Trip
Maybe it’s because I grew up watching Hocus Pocus and Gilmore Girls, but a fall road trip through New England has been high on my travel bucket list for years.
The fall foliage here is unmatched. I say that as someone who leaf peeps every year across the U.S., nothing compares to the golden valleys and red-drenched mountains of Vermont and New Hampshire.
Add in covered bridges, charming towns, cozy inns, cider mills, and a whole lot of maple syrup… and you’ve got the perfect autumn trip.
When to Plan Your New England Fall Road Trip
The trickiest part of planning a New England fall foliage road trip is timing it right. Too early and the trees are still green. Too late and you’ll hit Stick Season, and while the Noah Kahan song is catchy, the brown bare trees aren’t quite the vibe.
Peak foliage usually runs from the last week of September through the second week of October. Use a foliage tracker to monitor live updates.
Pro Tip: Book early! I planned our girls’ trip in August and was scrambling to find available hotel rooms. Ideally, you should book flights, hotels, and a rental car no later than June.
Fly into Boston for the best route. It’s easier to find affordable flights, and you can drive to towns like Woodstock or Stowe in just a few hours. Everything is so close together, making this a manageable day itinerary with several 2–3 hour drive segments.
New England Fall Map
My Exact New England Fall Road Trip Itinerary
Use this itinerary as-is or customize it to fit your schedule. Here’s where we stopped and why it was magical.
Stop 1: New Hampshire & The Kancamagus Highway
We flew into Boston from San Francisco, picked up our rental car, and drove 2.5 hours to Conway, NH.
The Kancamagus Highway (“The Kanc”) is one of the most iconic fall drives in the U.S.A must for any New England road trip. It’s packed with scenic overlooks, waterfalls, and dense forest painted in autumn colors.
Where We Stayed In Conway
- We stayed at Merrill Farm Inn, a charming country inn with a cozy, farmhouse vibe.
- Next time I would probably book this adorable A-frame Airbnb near Conway since it’s super cute.
For dinner that night we ate at the Sea Dog Brewery and discovered the magic of sugar on beer rims. It’s apparently a New England thing.
Tip: Bring Snacks And Cash
Bring at least $10 in cash as some areas require a day use fee and you can get fined if you don’t pay. There’s also no rest stops or gas stations along The Kanc, so I recommend you stock up on snacks for your road trip.
We bought a lot of gatoraide, coffees since we had a lot of early starts, granola bars, dried fruit, etc.
Must-Do Stops on the Kanc:
- Sabbaday Falls (tall waterfall, easy walk)
- Rocky Gorge Scenic Area (stunning in the early morning)
- Falls Pond (great with the drone!)
- Albany Covered Bridge (pack a cute outfit for this one!)
- Hancock Overlook (go at sunrise for drone shots)
- Russell-Colbath House Cemetery for spooky vibes
- Loon Mountain Resort (take a lift ticket up for great views and grab food at the top of the mountain!)
- Optional detours to Dixville Notch and Franconia Notch State Park
Pro Tip: Get up early. By 10 a.m. on Saturday, we hit a full-on traffic jam but we started at sunrise so we had almost finished our drive. Aim to hit the road at dawn. For real. You can nap later.
Other Tips:
- Ride the Conway Scenic Railroad if you have an extra day. Next time I want to ride this since I love trains!
- Book Flume Gorge tickets in advance (we didn’t and couldn’t get in).
Off-The-Kanc Suggestions:
- Artist’s Bluff Loop Trail: Moderate, dog-friendly hike with epic views.
- Polly’s Pancake Parlor: Stop for pumpkin donuts or breakfast (there may be a wait).
- Great Vermont Corn Maze: Worth a stop if timing works.
Stop 2: Littleton, New Hampshire
Just over the state line from Vermont, Littleton is another charming New England town that makes a great detour or stopover after driving the Kancamagus or before heading to Franconia Notch State Park. We stopped by here for breakfast after not being able to get into Polly Pancakes and loved it.
Why You Should Visit Littleton:
- Downtown Vibes : Littleton has a walkable downtown filled with diners, boutiques, antique shops, and—if you time it right, like a weekend farmers market with local produce, baked goods, and handmade crafts.
- Covered Bridge in Town: Yes, there’s a covered bridge right in downtown! It’s a beautiful photo spot, especially in October when it’s framed by peak foliage.
- The Coffee Pot Restaurant or Littleton Diner: Great for a casual lunch or diner-style breakfast.
- Antique Stores: If you’re a vintage lover, you’ll want to carve out time to poke through the antique shops. You never know what fall-themed treasure you’ll find.
Littleton is less touristy than other fall destinations in New England, which means easier parking, no wait at brunch, and that cozy, small-town atmosphere that makes autumn in New England feel so magical.
Stop 3: St. Johnsbury, Vermont
If you’re passing through Northern Vermont on your way between the Kancamagus Highway and Greensboro or Stowe, make time for a stop in St. Johnsbury. This small town surprised me with its charm and delicious fall treats, it’s a perfect pit stop for leaf peeping road trippers who want a cozy, low-key break.
We saw it from a distance and all agreed we had to explore the town and I’m so happy we did!
Things to Do in St. Johnsbury:
- The Buttery: Grab a latte and a pastry (trust me, they’re so good) and pop into the curated gift shop next door for cute, locally made finds.
- Boule Baker: Another great option for baked goods, and everything has that homemade, just-out-of-the-oven taste.
- St. Johnsbury Athenaeum: Even if you’re not a library person, this historic public library is worth a quick peek. It’s stunning inside and gives you that classic old New England town feel.
This town has great fall colors, photogenic streets, and fewer crowds than places like Stowe. It’s a great option if you’re chasing peak foliage and want a relaxed, photogenic place to stretch your legs and grab a snack.
Looking to spend the night near St. Johnsbury? I found this really cool A-frame Airbnb that would be so fun to stay at.
Stop 4: Highland Lodge, Greensboro, VT
Our next stop was the Highland Lodge in Greensboro, Vermont, a rustic-chic hotel with lakefront views and serious old New England charm. I loved this place and can’t wait to come back with my husband one day.
Why We Loved It:
- Private lake access with free kayaks & canoes
- Cozy, historic main house plus rentable cabins
- STUNNING sunsets
- Delicious farm-to-table restaurant (order the honey cardamom duck)
- Relaxing down day after our Kanc adventures
You could also explore nearby cideries or shops, but honestly, we used this stop to slow down, paddle on the lake, and drink wine in their cozy dining room.
Stop 5: Stowe, Vermont
No New England fall foliage trip is complete without a few days in Stowe.
This charming mountain town is packed with scenic drives, maple lattes, cozy cafes, corn mazes, and iconic fall photo ops. Our days spent in Stowe were my favorite. If anything, I would recommend spending an extra night here since there’s just so many fun coffee shops, corn mazes, nearby hikes and sights to see.
Top Things To Do in Stowe:
- Percy Farm Corn Maze: Fun, low-key, and only $8. They also usually have farm animals to pet.
- Trapp Family Lodge: Happy hour with Sound of Music views. Get the martini and sit outside at sunset!
- Black Cap Coffee: Get the maple croissant. Trust me. I would fly back to Vermont just for this croissant.
- Downtown Stowe: Great for shopping, photos, snacks.
- Gold Brook Covered Bridge: Picturesque and quiet.
- Stowe Gondola Skyride: Expensive but worth it for the foliage views. Get there early!
- Cold Hollow Cider Mill: Cider donuts, apple cider, maple sriracha (so good). Gets crowded on weekends so come early.
- The Butler’s Pantry: Hidden gem dinner spot with a great view of the church.
- Smuggler’s Notch Drive: Epic leaf peeping route.
- Mount Mansfield Hike: 7.5-mile hike to Vermont’s highest peak.
- Ben & Jerry’s Flavor Graveyard: Quirky roadside stop on your way to Woodstock.
- Stowe Recreation Path: Easy, scenic bike ride.
Where We Stayed:
- Bluebird Cady Hill Lodge: Cozy, modern mountain lodge with hot tub, fire pits, and a perfect fall vibe. Book early!
- Awol Stowe: Sister property with A-frame cabins and a cedar hot tub. We got a chance to go inside one and it’s beautiful.
- A-frame Airbnb: If you’re a cabin girl, you’ll love this adorable chalet a-frame near Stowe on Airbnb.
Stop 6: Woodstock, Vermont
We didn’t stay overnight here, but I would next time. Woodstock is one of the most beautiful and charming towns in New England.
Things to Do:
- Walk down Pleasant Street (Instagram-famous white fence + pumpkins)
- Stop at Sugarbush Farm for maple syrup tasting & Vermont cheese (almost as good as Wisconsin… almost)
- Explore Sleepy Hollow Farm (a dreamy photo spot near Woodstock with classic New England fall colors – just make sure to check local road blocks, some years they’ve been blocking the road down off from tourists.)
- Pop into local shops and enjoy the historic town vibe.
Stop 7: Salem, Massachusetts
We ended our trip in Salem, where the fall vibes shift from foliage to full-on spooky, and a little urban. We made sure to plan our Salem trip for a Tuesday night, so we were there in the middle of the week instead of risking the crowds on the weekend.
And honestly, it was great. We arrived Tuesday night and other were people out on the Essex Street but nothing like the sardine-packed videos I’ve seen on social media. We walked around at night when all the Halloween decor was up, and then had dinner at Turners.
The next morning, we visited a bunch of Hocus Pocus sights around Salem and Marblehead, and then explored the downtown Salem area by day to pop into spooky cafes and museums. After so much driving around fall sights, it was nice to just park the car and walk everywhere.
Things to Do:
- Witch Museum
- Hocus Pocus filming locations
- Pioneer Village, Bewitched Statue, Salem Commons
- Wynott Wands (for Harry Potter fans)
- Count Orlok’s Nightmare Gallery (for horror film buffs)
- Hawthorne Hotel (haunted and historic!)
Pro Tips for Visiting Salem:
- Avoid weekends and Halloween day. Way too crowded.
- Best days to visit: Tuesday or Wednesday
- Explore Essex Street at night and again during the day for two totally different vibes
Where We Stayed In Salem
- Hampton Inn Salem Boston: This hotel was super expensive since we booked last minute, but it’s literally a couple blocks from Essex street so it was worth it. Traffic is insane here so you’ll want something in walking distance so you can skip ubers or cars.
- Witch Hallow Airbnb: next time I’ll be trying to book this near witchy Airbnb in Salem.
We ended the trip with lobster martinis, museum hopping, and shopping for witchy souvenirs—a perfect cozy-spooky finale.
Route Map & Logistics
- Rental Car: Needed for most of the trip (not Salem).
- Driving: Boston to Conway (~2.5 hrs), Conway to Greensboro (~2.5 hrs), Stowe, Woodstock, then Salem.
- Playlist: Make a fall road trip playlist (mine had a lot of Noah Kahan and social media favorites).
What to Pack for a Fall Road Trip
Autumn weather in New England is actually still pretty warm in the day, at least to our group who lives in San Francisco, where it’s 60’s year-round. There was an afternoon on our trip I was really hot and stripped down to t-shirts.
But, the mornings and evenings are chilly so if you are planning on any early morning hikes or sunrise leaf peeping, you’ll want a puffer jacket, thick sweater or a coat.
- Sweaters & flannels
- Hiking boots
- Comfy walking shoes like Teva for warmer days
- Reusable water bottle & portable charger
- Camera or smartphone with storage
- Cozy socks & beanie
- Swimsuit (if hotel has a hot tub or sauna)
- Small daypack or crossbody bag
- Your fave Kiel James Patrick leaf sweater
- Scarves and tall boots for that classic New England road trip look
Tips for Planning Your Own New England Fall Road Trip
- Book hotels & car by June or July (it’ll get harder in August and September but still doable!)
- Travel on weekdays to avoid leaf-peeping crowds. If you can only travel on the weekend, get up early each day.
- Mix scenic drives with slow town days for balance
- Track foliage with a reliable online tracker
- Fly into Boston and loop from there
- Include stops like Franconia Notch and Dixville Notch for extra beauty
FAQ About New England Fall Road Trips
How long should my trip be? 5–8 days is ideal. Next time I would actually come closer to 10 days with my husband and take it really slow, renting cute cabin or farm Airbnbs along the way. But, you can also do the trip in just a few days if you priotizie.
What’s the best state for fall foliage? Vermont and New Hampshire both shine. Vermont is more small-town charming, while NH has the best mountain views and access to places like The Kanc and Franconia Notch State Park.
Is this kid- or dog-friendly? Yes! Most towns are walkable and pet-friendly, but not all trails are dog-friendly. Check first.
Do I need to book hotels early? Absolutely. Fall is peak season in New England.
Estimated Trip Cost Breakdown
(Per person based on a 5–6 day New England fall road trip)
- Flights: $500–$800 roundtrip to Boston for the high season.
- Rental Car & Gas: ~$150–$200 pp
- Hotels: $600–$800 pp (shared rooms)
- Food & Drinks: ~$450
- Activities/Tickets: ~$200 (museums, gondola, corn mazes)
- Total Estimate: $2400 per person
How to Modify This Itinerary for 3–4 Days
Short on time? If a 7 day New England Fall Road Trip Itinerary is too long, you can still soak in the foliage magic in a few days.
Option 1 for short fall road trip in New England:
- Day 1: Boston early AM on a redeye then drive to to Lincoln/Conway and drive the Kancamagus Highway.
- Day 2: Explore Polly’s Pancakes, Artist’s Bluff, drive to Stowe.
- Day 3: Full day in Stowe, then drive to Boston in evening.
- Day 4 (optional): Salem day trip before flying home depending on your flight.
Option 2:
- Base yourself in Stowe or Woodstock for 2–3 nights and do scenic drives, cider stops, and hikes from one hub.
This is perfect for a long weekend fall foliage getaway.
Best Instagram-Worthy Photo Spots
If you’re planning to share your New England road trip on social media, don’t miss these photo spots:
- Hancock Overlook (Kancamagus) – sunrise drone views
- Albany Covered Bridge – classic New England charm
- Sleepy Hollow Farm (Woodstock) – peak foliage gold
- Pleasant Street (Woodstock) – white fence and pumpkins
- Percy Farm Corn Maze (Stowe) – fun fall vibes
- Trapp Family Lodge patio – golden hour mountain shots
- Cold Hollow Cider Mill – donut & cider cup pic
- Gold Brook Covered Bridge – postcard-worthy
- Stowe Gondola top view – iconic fall panorama
Final Thoughts: Why This Fall Trip Lived Up to the Hype
Some of my favorite moments:
- Canoeing at sunset at Highland Lodge
- Maple syrup tasting at Sugarbush Farm
- Solving the corn maze in Stowe
- Visiting Sleepy Hollow Farm at peak foliage time
There’s no National Parks in Vermont, but all the foliage there on the state parks and public drives are just stunning and make for an epic fall road trip in New England.
It’s a busy trip, one that will keep you busy since there’s just so many stunning fall drives to take, so many maple coffees to drink and pumpkin donuts. I felt like I couldn’t sleep since I didn’t want to miss out on the fall magic. I loved it.
If you’re thinking about planning your own fall road trip through New England, I recommend you don’t wait. Hotels book up quickly, but it’s so worth the effort. You’ll come home with a camera roll full of golden trees and a heart full of cozy memories.
Have questions about this guide? Drop a comment or DM me on Instagram @thewhimsysoul!
