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5 Day New England Fall Road Trip Itinerary

acadia national park in the fall

I still remember the rows of reds, oranges, and yellows lining the highway as my family and I drove up the I-84 last fall. I had just moved to New York City two months prior and was already in awe with all the scenery changes that come with the distinct four seasons. I can’t think of a better way to see fall foliage on the east coast than doing a New England fall road trip! Besides stunning foliage, there’s also good food, history, architecture, and hiking to fill up your itinerary.

My 5 Day New England fall itinerary starts in New York City, but depending on where you’re traveling from, you can take any segment of this and shorten or lengthen certain days depending on what you want to get out of your trip. This itinerary also assumes that you’ll be driving from and returning to New York City after the trip.

Table of Contents

Day 1: Head Straight from New York City to Portland Maine

Day 2: Explore Acadia National Park

Day 3: Watch the Sunrise at Cadillac Mountain

Day 4: Spend the Day in Boston

Day 5: Return Home!

Day 1: Head Straight from New York City to Portland Maine

viv the wanderer portland maine
Me very excited to be in Portland

You’ll do the bulk of the drive on day 1, spending 5+ hours on the road while witnessing the trees get redder and redder as you drive toward the colder regions.

Once you get to Portland, enjoy some delicious Italian food or seafood. There are so many great restaurants in Old Port especially.

Restaurants in Old Port for All Taste Buds

restaurants in old port portland maine
Outside of Via Vecchia
  • Street & Co: slightly fancier sit down spot. Some of the best pasta I’ve ever had!
  • Via Vecchia: another Italian spot that’s trendier than Street & Co and has a beautiful interior and exterior. Great spot for outdoor dining if the weather is nice.
  • The Highroller Lobster Co.: casual lobster restaurant that’s also family friendly. This place has nearly 3k reviews on Google Maps averaging 4.7 stars!

Regardless of where you choose to eat, try to make a reservation in advance to avoid waiting in line once you get there.

End the night by taking a stroll on the cobblestone streets in Old Port. There are small shops and bars that will keep you entertained for the rest of the night.

Day 2: Explore Acadia National Park

acadia national park new england fall road trip
Acadia National Park

After a night’s rest in the romantic city of Portland, you should be ready to see one of the most beautiful national parks during the fall – Acadia National Park!

Portland to Acadia is another 3 hour drive, so you’ll want to grab a quick bite in Portland on day 2, then head straight to the national park to make most of your day.

Enjoy Fresh Lobsters at Acadia Lobster & BBQ Co.

maine lobsters new england fall road trip
Acadia Lobster & BBQ Co.

About 15 minutes outside of the Acadia National Park visitor center, you’ll first come across a handful restaurants serving up fresh lobsters. Stop at Acadia Lobster & BBQ Co. for a hot plate with lobster, mac and cheese, and some cole slaw. It’s hard to get better lobsters anywhere else on the east coast!

Wanderer Tip: The lobster restaurants typically close up shop as the weather gets colder. When we visited late last October, we had one of the last lobsters served. If trying Maine lobsters is an important part of your New England fall road trip, plan your trip a little earlier to avoid missing your chance.

Drive the Park Loop Trail

This is the first of two days you’ll spend in Acadia National Park. So take the time on day 1 seeing more of it by driving along the Park Loop Trail. Do some research ahead of time or during your drive to decide which spots you want to make along the 27-mile scenic road.

My Top Trails in Acadia National Park

  1. Sand Beach
  2. Thunder Hole
  3. Jordan Pond House

The drive, plus any pit stops you make will surely work up your appetite for some more delicious seafood in the evening.

Have Dinner in Bar Harbor

After a day in the national park, find a dinner spot in the local town, Bar Harbor. I recommend Geddy’s, a casual American restaurant that serves lobsters and a mean blueberry pie, or Reading Room Restaurant, where you get to dine on a boat with incredible waterfront views!

Day 3: Watch the Sunrise at Cadillac Mountain

sunrise at cadillac mountain acadia national park
Cadillac Mountain Summit

What’s a trip to a national park without waking up at 5am in the morning to watch the sunrise? Start Day 3 bright and early by watching the sunrise at Cadillac Mountain.

You’ll get stunning views of fall foliage, and see silhouettes of the Porcupine islands as the sun comes up. It’s an absolutely stunning sight. Remember to grab a hot cup of coffee and dress in layers as it gets cold at the summit.

Once you’ve had enough of the sunrise, drive to Bar Island and spend about an hour or two hiking to the peak for another viewpoint of the national park.

The Bar Island Trail was one of the coolest things we did at Acadia National Park (and overall during our New England fall road trip!) A small “bridge” forms when the water surrounding the island is on low tide, allowing us to cross over to the island. Once it’s high tide again, the bridge disappears and you want to make sure you’re back before then otherwise you could get trapped on the island. The fact that we could get trapped added to the excitement of the hike.

Day 4: Head South to Boston

acorns street boston
Acorns Street

At this point in our New England fall road trip, we debated driving west toward Stowe, Vermont to see more epic fall foliage. But given it was going to be another 5 and a half hour drive we decided it was way too ambitious. And I’m glad we ended up heading straight to Boston.

There’s no “right way” to spend a day and a half in Boston, so I’ll share some of the top activities I’ve enjoyed during my trips there and you can piece together your own itinerary for this particular bit 🙂

Top Things to Do in Boston

  1. Admire the Isabella Stewart Gardener Museum. The museum itself is beautifully built, with a courtyard in the middle filled with plants and sculptures. It’s one of a kind and totally worth a visit while you’re in Boston.
  2. Tour the Harvard University Campus. Harvard is one of the world’s most famous universities after all. Have I said enough?
  3. Enjoy fresh Oysters at one of the many restaurants in downtown Boston. TimeOut has a whole article on oyster bars in Boston. Check it out here.
  4. Walk along the Freedom Trail: Get a quick history lesson on the American Revolution by walking along this 2.5-mile marked path.
  5. Visit Acorns Street. The cobble-lined street is one of the most photographed streets in Boston, and for good reason.

Day 5: Return Home!

The drive from New York City to Acadia National Park and back is no joke. You’ll want to take it easy on Day 5, grab a bite in Boston, and start journeying back to New York City.

If you’re feeling the energy for it, maybe make a quick pit stop in Providence so you can check one more city off your New England roadtrip bucketlist.

One of the Best Road Trips for Fall

Hopefully by the end of this road trip, you’ll have gotten a true taste of New England in the fall. It sure will be one road trip to remember.

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