10-Day Ultimate New England Road Trip

This 10-day New England road trip will take you on a scenic drive from Boston to Bar Harbor and vice versa.

For this trip, we flew into Bangor, Maine and drove down to Boston. You can easily swap the route and follow this guide as a Boston to Maine road trip itinerary.

Additionally, if the cost of flights are cheaper/makes sense for you, you could also fly into Portland, Maine and take a scenic drive to Bar Harbor. Or, even fly in & out of Boston, but add some more driving time to your plans.

What I love most about this Maine road trip is that you’re actually not spending that much time on the road. Some days you might have to drive 2 hours max, but most of the trips are even shorter. You can break up those drives even shorter if you want stopping in any of the coastal towns along your route. It’s no surprise to me why they call Maine “Vacationland.”

Day 1 – Start Your New England Road Trip

This day you’ll fly into Bangor, Maine (or Boston if you’re starting from the South) and heading to Bar Harbor.

I can’t imagine there are a lot of direct flights into Bangor, which was the smallest airport I’ve ever flown into. We had a layover in NYC, then a short flight to Bangor on a small plane. At the Bangor airport we rented our car and headed just a few miles into the town of Bangor to stop at Stephen King’s home.

I’m a book nerd. So, this stop was really fun for me and literally not at all out of the way to visit. You basically make a right off the main street in Bangor and you’ll be at SK’s home. We snapped a quick photo and got back on the road. Then you just hop back on the main street to the highway that takes you to Bar Harbor.

Bar Harbor will be the cutest town you’ve ever seen. Settle into your hotel or inn or Airbnb, etc and explore the walkable city center. You can walk along the water, rent bikes, explore the shops, and enjoy the scenery.

One option to round out the evening would be to catch the sunset on Cadillac Mountain inside Acadia or at the Bass Harbor lighthouse. The lighthouse is scenic, but Cadillac Mountain has the better views. You can drive up the mountain, but I’d recommend taking the free bus that runs or one of the paid buses since parking will be at a minimum.

Or, if you’re exhausted from the day’s travel, grab dinner at one of the restaurants in Bar Harbor and call it an early night.

Day 2 & 3 – Spend the Day in Acadia National Park

Get up and at ‘em early this morning. It’s time to head into Acadia. If you want to drive yourself you need to be in the park by 8 am or parking will just get more and more difficult. Take a lesson from me and opt for one of the free or paid buses.

What to do in Acadia National Park:

There are endless ways to entertain yourself in Acadia. You can take a scenic drive and stop off at ample viewpoints, go for easy to moderate to super challenging hikes, have lunch and popovers at Jordan Pond House, ride bikes along the pathways, go rappelling, kayaking, and even visit a beach.

If you’re not big on the outdoors, you could just spend one full day in Bar Harbor & Acadia. You could also extend this part of the trip and stay another day too.

You’ll be exhausted after a day in the park. I’d recommend going for pizza & beer in Bar Harbor and finishing it off with some ice cream. You only have to walk five feet to find an ice cream place in Bar Harbor.

Day 4 – Head to Rockport, with a stop in Camden

Views from Mt. Battie on the left, views from our sail on the right

Today you’ll head to Rockport with a quick stop in Camden. My favorite part of this trip is that none of the drives are really that long. And you can easily break them up and stop at any of the towns along the coast. We decided we would stop in Camden for a light lunch and a quick hike. The Camden State Park has a really fun & pretty quick hike up to Mt. Battie.

The hike took us about an hour. It was much less crowded than Acadia even in the middle of summer. We saw a few other small groups, but it was a nice, peaceful and fun hike. There is a pretty steep incline near the beginning, but it doesn’t last long and there are lots of places to stop and catch your breath. There is plenty of shade throughout this part too and near the end you’ll have a long mostly-flat path.

From Camden to Rockport it was only a short 30 min drive. We checked into our Airbnb (this place!!) and grabbed some wine from the storefront to bring with us on a sunset sail. Sail Heron was our sunset sail of choice.

I loved Rockport and, if you wanted, I think spending another day here could be very relaxing. You could travel nearby for a hike or get back out on the water again. And enjoy some of the amazing restaurants nearby. Next time I’m on the Maine coast I do plan to stop in this cute town.

READ NEXT Things to Do in Rockport and Rockland

Day 5 – Head to Portland with a stop at LL Bean

Today, you’ll make the trek to Portland with a stop at the LL Bean flagship store. We actually took one of the stand-up paddle boarding classes here. They offer tons of classes and activities at really reasonable prices. And if you take one of them you’ll get a card for a discount at the store that you can use after. Even the store has free entertainment running with live music and other activities. It’s honestly pretty amazing and worth the stop.
Sidenote: If you’re going to get fast food at any point during the trip – this is the spot. One of the fanciest McDonald’s is located here in Freeport.

After this, head to Portland. Check into the hotel and wander out for dinner in the city. We freshened up and were able to stop at Mr. Tuna for a quick bite before it closed then visited one of their many breweries and got the potato donuts from Holy Donut which were absolutely delicious & alone made the trip worth it. HAHA. We ended with dinner at Portland Lobster Company so we could get our lobster fix. Be prepared to wait.

Day 6 – Spend the Day in Portland

No driving today. You’ll spend the entire day in Portland!

What to do in Portland, ME:

Take a tour, rent bikes, brewery hop, get out on the water, visit the beach, visit the lighthouses. Eat lots of good food like donuts, oysters, lobsters, sushi and whatever culinary delights you can find. Contemplate moving here just to have Holy Donut on the regular.

Day 7 – Head to Kennebunkport & Salem

Now, it’s time to head out of Maine. Our next destination was Salem, but we decided to stop in Kennebunkport on the way for a late breakfast and to break up the drive.

Kennebunkport is the perfect stop for a few hours on your Maine road trip. We walked along the main strip and popped into some of the shops and enjoyed the views. We ended with a brunch at The Burleigh and ice cream to go from Rococo. I swear I don’t eat ice cream often when I’m home, but we have it all the time on vacation.

Now, head down to Salem. We checked into our hotel first, just outside the city. We stayed at the Marriott Peabody. I was able to cover the stay with not a lot of points. It was clean, quiet and had friendly staff. Plus, there was a hot tub, pool and free breakfast!

Considering cost & convenience, it made sense for us to stay outside of Salem. It was only a short drive back after exploring the town and the next morning it made it even easier to get into Boston.
Depending on the time of year you visit, you can see a lot of Salem in a half-day or full-day visit. If you lived nearby, it would make the perfect day trip. Since we were there in the summer, there were definitely fewer crowds than say in October, but there’s still plenty to see.

If you’re trying to shorten your trip, you could go straight from Portland to Boston. (Only about a 2 hour drive).

What to do in Salem, MA:

Walk the Red Line, visit the Salem Witch Museum, enjoy dinner and try a haunted walking tour.

READ NEXT: 13 THINGS TO DO IN SALEM, MA

Day 8 & 9 – Head to Boston and Sightsee

Now we’re off to Boston. If you felt like you needed more time in Salem, you could definitely spend the morning there again before heading to Boston.

We decided to return our car at the Boston airport since we’d be able to walk most of Boston & didn’t want to pay to park it at the hotel. (Parking costs in Boston are super expensive!) This process did take up a good chunk of our morning so by the time we made it back to our hotel and checked in, we were ready for lunch. Bartaco was a convenient spot right by our hotel.

If you’re visiting Boston in the summer like we did, there’s a chance it will be hot and humid and stormy. This was the case for us so having the two full days to explore was helpful. We took breaks at our hotel during the hottest part of the day.

Beyond that, we did lots of exploring.

What to do in Boston, MA:

Visit museums. Explore Little Italy and eat some pizza, pasta and cannolis. Pizza at Umberto Galleria is $1.90 for a big slice! Explore Harvard. Rent a paddle boat on the water. Take a walking tour of the Freedom Trail and learn all about the history in this one town. Visit Envoy Boston Hotel for some great evening views and cocktails.

Day 10 – Your New England Road Trip Ends

It’s time to head home. I recommend grabbing breakfast in the city before flying out. We loved Flour Bakery.

This New England, Maine & Massachusetts summer vacation was one of my favorite trips. The entire time I was thinking about how I couldn’t wait to return someday. If you have any recommendations for other towns to stop in, sights to see, food to enjoy, please leave a comment below! I’ll add them to my itinerary for next time. 🙂

And you can save this post to Pinterest using any of the images below.

This New England Road Trip itinerary takes you from Boston to Bar Harbor and vice versa. Drive scenic routes through Maine, stopping in Portland and more.
This New England Road Trip itinerary takes you from Boston to Bar Harbor and vice versa. Drive scenic routes through Maine, stopping in Portland and more.
This New England Road Trip itinerary takes you from Boston to Bar Harbor and vice versa. Drive scenic routes through Maine, stopping in Portland and more.
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