Updated: Aug 28, 2023
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I still remember the rows of reds, oranges, and yellows lining the highway as my family and I drove up the I-84 in fall of 2021. 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 driving up from New York City to Acadia National Park! 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 1: Head Straight from New York City to Portland Maine
You’ll do the bulk of the drive on day one, 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, Portland for All Taste Buds
- 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. And if you decide to eat on a patio, make sure you’re dressed appropriately as it can get chilly by the water.
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
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.
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 in late October, we had one of the last lobsters served. If trying Maine lobster is an important part of your New England road trip itinerary, plan your trip a little earlier to avoid missing your chance the delicious crustacean!
Drive the Park Loop Trail
This is the first of two days you’ll spend in Acadia National Park. When I only have two days at a national park (this was the case during our U.S. cross-country road trip and when we visited Volcano National Park), I like to spend the first day taking as much of the park in as possible, and do deeper explorations on the second day.
The Park Loop Trail is the perfect way to see as much of Acadia as possible. After all, you already spent so many hours driving up to Acadia from New York City, you’ll want to see as much as possible. Do some research ahead of time or during your drive to decide which stops you want to make along the 27-mile scenic road. You can also pay a little bit for an audio guide of Acadia National Park from GyPSy guide that will shed light on your surroundings as you drive through the park. It’s one of my favorite apps to use whenever I visit a U.S. national park.
Top Trails in Acadia National Park
1. Sand Beach
Yes you read that right. There are beaches in Acadia National Park! When I first found out that that was a thing, I thought it was so unique. Besides perhaps Hawaii, I only ever expect to see hiking trails and viewpoints at national parks. But not at Acadia. Besides Sand Beach, Echo Lake Beach is another fun place to check out.
2. Thunder Hole
Thunder Hole got its name because of how the waves sound when they crash against the cliffs in this rocky part of the national park. But you’ll have to time it right to see nature do its wonders at this stop in Acadia. Per the National Park’s website, you’ll want to arrive 1–2 hours before high tide for the best chance at hearing the roar.
3. Jordan Pond House
A great place for lunch or a coffee, Jordan Pond House is located along the Park Loop Trail by the Jordan Pond Trailhead. The trail is a super easy loop around Jordan Pond and is a great place to take a stroll after you’ve had a snack or meal at the pond house. I didn’t get to try it when I was there, but apparently the popovers are the thing to get there.
Wanderer Tip: I’ve found the best way to research a trail ahead of time is using the AllTrails app.
Have Dinner in Bar Harbor
The drive from New York City, plus any pit stops you make within Acadia National Park will surely work up your appetite for some more delicious seafood in the evening.
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
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
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
- 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.
- Tour the Harvard University Campus. Harvard is one of the world’s most famous universities after all. And if you don’t care about that, at least go and see the campus Legally Blonde was based off of!
- 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.
- Walk along the Freedom Trail: Get a quick history lesson on the American Revolution by walking along this 2.5-mile marked path.
- 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 bucket list.
NYC to Acadia: 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. If you still didn’t have enough after this trip up to Acadia National Park, you might be interested in reading about spending fall in west coast’s Portland, a.k.a. Portland Oregon, another EXCELLENT road trip destination for fall.
