Skip to content

The Ultimate 9 Day New England Fall Roadtrip

Disclosure Policy: Some links are affiliate links meaning I may make a small commission at no cost to you. I appreciate your support!

Epic 9 Day New England Fall Roadtrip Itinerary

The most iconic way to enjoy fall in the United States is on a New England Fall roadtrip. While it can be tough to time peak foliage, the general rule of thumb is late September and early October are the best weeks. We did an iconic 9 Day New England Fall road trip itinerary the first week of October and were just ahead of peak in some places but caught it right on in New Hampshire. Unless you have multiple weeks to spend in the area to chase peak colors, you’ll probably hit some places right at peak, some places early and others past peak. Being flexible is the best mindset!

I still dream of this trip and since many others do too, it’s best to book early (like 6 months out) to secure your top accommodations, especially for the weekends. That being said, we booked this trip about 3 months out and still ended up with fantastic accommodations, although we had to be flexible on dates. Read on for an iconic 9 day New England Fall Road Trip itinerary!

Things to Know for Planning:

  • Book early, including your car rental
  • As opposed to staying in different cities like we did, you could also base yourself in the center of all the places you plan to visit (e.g. around Stowe) and visit these regions as day trips
  • Bring a headlamp just in case you hike early or late since the sun rises later and sets early this time of year
  • Bring a small cooler for treats you pick up along the way (I wished for this on more than one occasion on this trip!)

Day One: Boston

One of the best and least expensive airports to fly into is Boston.  We chose to spend a full day exploring Boston since it’s an iconic city and loved our time there.  For what to do over 24 hours in Boston, read here.

Where to stay: Hotel Indigo – very well located, beautiful rooms and great staff!

Epic 9 Day New England Fall Roadtrip Itinerary

Day Two: Boston to Burlington Vermont

Start your drive to Burlington from Boston and stop en route in Woodstock (~4 hours driving time).  Woodstock is iconic for many reasons and three fun stops in the fall are:

  • Sugarbush Farm (Make sure to buy some Grade A Vermont Maple Syrup and sample the cheese!)
  • Sleepy Hollow Farm (This is someone’s residence so respect their fences when taking photos. It gets really busy with others on their New England Fall roadtrip too)
  • Taftsville Covered bridge

Continuing on to Burlington for the night, grab dinner from the amazing Hong’s Chinese Dumplings (which were once sold from a cart but moved to a storefront so people can enjoy them year-round!) and enjoy local cider from Citizen Cider. Don’t miss the turmeric cider if it’s available!

Where to stay: Best Western Windjammer. This hotel is just outside of the main Burlington area and offers comfortable rooms, a great included breakfast and both an indoor and outdoor swimming pool. We loved it as our base!

Day Three: Burlington to Stowe Vermont

Start your day exploring around Burlington. The city is a really fun college town with great restaurants and a view of New York across the beautiful Lake Champlain. For a fun morning:

  • Grab coffee from Muddy Waters (it’s super eclectic inside and the drinks are delicious!)
  • Enjoy a bonut (part biscuit, part donut) from The Café Hot
  • Rent bikes to cycle on the lakeside path
  • Enjoy a maple creemmee from the lakeside stand
  • Sample beers at Foam Brewers
  • Pick up a bagel sandwich from Burlington Bagel Bakery

(yes all of this can be done in a a morning 😊 )

Once you’re ready to leave Burlington, drive to Stowe via Smuggler’s Notch.  This is one of the prettiest drives in the region with lots of fun stops along the way.

Once in Stowe, definitely stop at the iconic Cold Hollow Mill for cider, donuts and apple goods. One of the best stops on a New England fall roadtrip!

If you’re still wanting more treats, head to the Ben and Jerry’s headquarters in Stowe for the freshest ice cream. Then enjoy a pizza dinner from Piecasso and ciders from Stowe Cider.

Where to stay: Timberholm B&B – a quintessential and stunning Vermont home. The rooms are so cozy, the common space living room is beautiful and comfortable, the breakfast served in the morning looked and tasted gourmet and there’s even a hot tub underneath string lights to relax in after your busy day exploring. HIGHLY recommend!

Day Four: Stowe to Lincoln New Hampshire

Start your morning in Stowe by walking the paths in town, taking the Gondola SkyRide to see even more stunning colors from a higher vantage point and grabbing delicious drinks from Vermont Artisan Coffee & Tea. We loved their coffee bar and the area to drink our coffee / tea outside overlooking the fall foliage! 

Afterwards, head to Lincoln and stretch your legs on a scenic hike at Mt. Willard in Crawford Notch. It’s pretty steep on the way up and despite only being 1.8 miles each way, it took us about 90 minutes roundtrip with plenty of stops for photos including at a little waterfall!

For dinner, check out The Common Man. It felt like a quaint British pub!

Epic 9 Day New England Fall Roadtrip Itinerary

Where to stay: Woodwards White Mountain Resort. The rooms are modern, the resort has views of the mountains, breakfast is included in your stay and a there’s beautiful outdoor space including a pool and outdoor games. It’s very well run and is even dog friendly! Another popular city to stay is Conway which is on the eastern side of the White Mountains.

Day Five: Lincoln to Acadia Maine via Dixville Notch

Start your morning in Lincoln EARLY because the hikes around here are VERY popular with people on a New England fall roadtrip! First, drive the Kancamagus Highway – there are many scenic places to stop on the way.  Our favorite was the Lincoln Woods Trailhead that has a beautiful bridge leading you to hikes. We just explored a little bit beyond the bridge since we had a few additional stops to make this day. You’ll have to pay to park in the lot – they have envelopes available to leave cash.

Epic 9 Day New England Fall Roadtrip Itinerary

After driving along the Kancamagus highway, head to Artists Bluff for one of the most iconic New Hampshire view points. Park at the Echo Lake Beach lot and then walk along Profile Road towards highway 93 and look for the trailhead on the north side of Profile Road.  This is a very direct route up to the viewpoint and is quite steep. You can also do a slightly longer loop (as shown at the link above) if desired which starts further west along Profile Road.  We did the full loop and spent about 60 minutes on this hike including time for photos/videos.

From here, head north to Lancaster for a quick lunch stop and to view a beautiful covered bridge. We enjoyed delicious sandwiches, salads and warm beverages at The Granite Grind.

Continue North to one of the most stunning Fall hikes in New England: Tabletop Rock. It’s listed as a Moderate hike and it’s well worth the uphill trek for the stunning view. Just be very cautious once on the rock and only do what you’re comfortable with. We spent about 90 minutes on this hike.

After the hike, continue driving east and you’ll see the stunning lake you saw from Tabletop Rock. It’s worth the stop to see the colors reflected on the lake.

From here, we drove all the way to Bar Harbor for our stay at the amazing Terramor glamping resort. If I could do this day over, I probably would have stayed near Tabletop Rock for the night but we were trying to make good time at Acadia so continued on.

Where to stay: Dixville Notch or continue on to Bar Harbor and stay at Terramor. It’s pricey but they truly have thought of everything and it feels like camp for adults. I also loved their breakfast included at the lodge, outdoor swimming pool and hot tub and included activities like stargazing and yoga.

Day Six: Bar Harbor Maine

Start your day with a leisurely breakfast (if you’re staying at Terramor, it’s included) before heading into Bar Harbor. There are many fun shops to explore before enjoying lunch in town. We checked out Side Street Cafe for delicious fish sandwiches and clam chowder (when in Maine!). We took ours to go and sat along the water. From our lunch spot, we saw people on an organized kayak tour so check into it if that’s something you’re interested in!

Now it’s time to head to Acadia National Park! We did the leisurely out and back Ocean Path Trail and watched sunset from the park before heading to dinner to get a good feel for the park before more intense hikes tomorrow.

For dinner, check out a restaurant along Main Street in Bar Harbor. Some places on our list we didn’t get to were: Peekytoe Provisions, Project Social Kitchen & Bar and Bar Harbor Lobster Co.

Day Seven: Bar Harbor Maine

After breakfast, swing by Mother’s Kitchen to pick up sandwiches you can enjoy later in the day for lunch on a hike in Acadia National Park.

Epic 9 Day New England Fall Roadtrip Itinerary

Start your day at Acadia with the popular Beehive Trail. I was very nervous before we did the trail based on reviews but I didn’t find it scary at all. There are plenty of ledges so I felt comfortable but if you have a fear of heights, definitely consider if you’d be comfortable on this hike. It was a super stunning and fun hike with amazing views!

Epic 9 Day New England Fall Roadtrip Itinerary

Afterwards, head to Jordan Pond to enjoy your lunch lakeside. If you want to try the famous popovers from the Jordan Pond Restaurant, get your name on the list and then hike up to Bubble Rock via the Jordan Pond Path to make your wait time more fun/efficient. During our visit, the wait time was 90 minutes for a table outside which was exactly what we needed to hike up to Bubble Rock and back at a good pace. If the wait time is less, consider doing the hike after your meal and just enjoy walking along the lake.

Epic 9 Day New England Fall Roadtrip Itinerary

At the restaurant, definitely get the popovers, lemonade and the popover sundae! Everything else sounded good too but we needed to save room for dinner at The Travelin’ Lobster. We went straight there from the park since it’s a popular dinner spot especially with others on a New England Fall roadtrip. Plan on waiting in a line (like possibly over an hour) – it’s worth the wait!

Epic 9 Day New England Fall Roadtrip Itinerary

Day Eight: Acadia to Portland Maine

Epic 9 Day New England Fall Roadtrip Itinerary

Start your day with an epic Sunrise at Cadillac Mountain. Make sure to reserve your spot in advance – it’s a nominal fee but they want to ensure it’s not too crowded. Pack lots of warm clothes and a blanket – it’s chilly on those fall mornings.

For one last adventure in Acadia National Park, check out the extensive Carriage Roads. We parked at Jordan Pond and walked some of the trails from there. The carriage roads were donated by John D. Rockefeller Jr. for city people to enjoy motor free scenic passageways. Today, you can bike or just walk them like we did.

Epic 9 Day New England Fall Roadtrip Itinerary

After leaving the park, stop back in Bar Harbor for lunch. We loved the smoothies from Thrive especially since we wanted a lighter lunch. We then continued on to a tasting at Atlantic Brewing – highly recommend!

From here, drive on to Portland Maine (about a 3 hour drive). We took the slightly longer (by 10 minutes) no toll route which was very scenic but you could also hop on 95 to save 10 minutes.

In Portland, we stayed at the beautiful newer Hotel Canopy which is very centrally located. The rooms are stunning, there’s a great rooftop restaurant and breakfast cafe on site, beautiful gym and the staff are super helpful. Highly recommend!

After checking in to your hotel, head over to Washington Avenue which is full of amazing restaurants, breweries and cideries. We had appetizers at Island Creek Oysters (SO good!), and pre dinner drinks at Maine Mead Works. There are many more spots to explore but we had dinner reservations back at our hotel’s rooftop restaurant – Luna – which was delicious. Luna had heaters and blankets so we stayed warm on a cool evening.

If you have more energy, head to Blyth & Burrows for drinks. We walked past it and it looked amazing!

Epic 9 Day New England Fall Roadtrip Itinerary

Day Nine: Portland Maine

On the final day of your New England Fall roadtrip, enjoy breakfast at Saltyard before driving to the super scenic Portland Head Lighthouse. It can be very windy so dress warm! We loved exploring the coast line before enjoying one more lobster lunch from the Cousins Main Lobster food truck on site. Also, don’t miss out on the whoopie pie – it’s the official dessert of the state of Maine!

After lunch, we drove back to Boston to catch our flight home to Minnesota. If we had had more time, we would have stayed one more night in Portland Maine. The food scene there is incredible and we’d love to return just to try more spots!

Ready to book your New England Fall roadtrip?!

For more US travel, check out my guides here!

Posted in

You may also enjoy...

Scroll To Top