Easy Boston to Bar Harbor Road Trip

Looking for road trip inspiration in the New England states? Look no further than a Boston to Bar Harbor road trip. Boston’s location in the northeastern United States makes it the perfect city to fly into and road trip from. My daughter and I took a day to drive up the coast, as part of a four day road trip that included Acadia National Park and the White Mountains of New Hampshire. You can read about our Two Days Acadia National Park, meanwhile, here’s the places we stopped in on the way to Bar Harbor.

Boston, MA to Portsmouth, NH

62 miles
1 hour

Our fly and drive July road trip started when we flew to Boston from Atlanta. We would’ve loved to explore Boston some but this trip was more about the road trip and Acadia National Park.

Once we picked up our rental car at Boston Logan International Airport, and after stocking up on food and the always important snacks, we headed north.

Since it was summer, I had counted on warm, sunny weather. The plan was to take US Route 1 and some of Hwy 1a as much as possible. Unfortunately, the weather wasn’t cooperating. It was raining really hard as we left Boston and it was easier to take Interstate 95, knowing we wouldn’t be able to make as many stops in the rain. Hopefully we would get some breaks in the weather and we did. After about an hour of driving, we exited the interstate at exit 3, Route 33 for our first view of New Hampshire: Portsmouth.

Portsmouth, built on the Piscataqua River, is a charming town with houses that date all the way back to the 1700’s. As you cross the river into town, to the east is the Portsmouth Naval Shipyard and to the west, the USS Albacore Museum, where you can tour a unique naval submarine. We didn’t really do much other than pass through since we were headed to Kittery, Maine, but the museum would be a perfect stop for this leg of a Boston to Bar Harbor road trip.

Portsmouth, New Hampshire

• Stay – The Port Inn & Suites
• Eat – The Portsmouth Brewery
• Coffee – Kaffee Vonsolln

Portsmouth, NH to Kittery, ME

2 miles
7 minutes

Cross the the river again, from Portsmouth on the World War I Memorial Bridge, and you’re in Kittery, Maine.

Kittery was settled by the English in 1623 and is the oldest city in Maine. It’s kind of ironic that now, most people stop for the shopping outlets than the historical features. For a little shopping and history, Kittery has a very popular Trading Post that’s been around a long time. Not as long as the houses but they have been in business since 1938.

If there’s anything you need to pick up for your trip or any outdoor equipment you want to buy, the Kittery Trading Post is the place for that. They have just about everything you can imagine and a few things you probably didn’t.

We ended our visit to Kittery by walking around downtown and grabbing some wood fired pizza at AJ’s Wood Grill Pizza. I would’ve loved to visit the Strawbery Banke Museum. The museum has more than ten acres of gardens, historic buildings and collections devoted to 300 years of American History. Saving that for another visit and better weather.

Kittery, Maine

• Stay – Hampton Inn & Suites Kittery
• Eat – besides AJ’s Rudder’s Public House
• Coffee – Lil’s Cafe

Kittery, ME to Ogunquit, ME

15 miles
23 minutes

I love the ocean and being so close to it without actually seeing it was driving me crazy. Bad weather or not, I wanted to walk on a real Maine beach.

So, from Kittery, we drove US Route 1 to Ogunquit, population 892. The unusual name, Oqunquit, means beautiful place by the sea in the Abenaki Indian language. And it is beautiful, even in the rain. Ogunquit Beach sits between the Atlantic Ocean and the Ogunquit River. The nearby cliffs and lighthouse offer sweeping coastal views of the dunes and waterfront.

The main public beach was surprisingly crowded for a cool, drizzly July day. Most people were cozied up, in comfortable chairs under a long covered sitting area that faces the beach. It looked like the perfect spot to read a book. All they needed was a fireplace to warm up. Wet and cold, we hurried back to the car to put the heat on. Even with the sun not shining, this was still one of my favorite stops.

For other things to do in Ogunquit, consider the Ogunquit Heritage Museum to learn more about the area. South of the beach is well-liked Perkins Cove, full of shops and restaurants.

Ogunquit, Maine

• Stay – Gorges Grant Hotel
• Eat – Ogunquit Beach Lobster House
• Coffee – Cove Coffee

Ogunquit, ME to Kennebunkport, ME

12 miles
23 minutes

Heading north from Ogunquit, we drove Route 9 into Kennebunkport. When I think about Maine, Kennebunkport is just the kind of place I picture in my mind. Lots of sidewalks, a cute historic district and plenty of colorful houses surrounding the water. Quintessentially Maine.

We didn’t do more than drive through but I at least wanted to see a bit of it. Especially since it’s been special enough for presidents to vacation there for years. And not just for presidents. Kennebunkport is a very popular destination in the summer months. The historic downtown was overflowing with people.

From downtown, we continued on Route 9 towards the coast and the village of Cape Porpoise Harbor. This area is considered the quiet side of Kennebunkport. It’s beautiful and peaceful with brightly colored fish houses in the coves.

I kept hoping the weather would clear so we could continue on Route 9 and make a few more beach stops. This route along the coast passes Goose Rocks, Drakes Island and Fortunes Rock, before it meets the Saco River and turns west. But the rain continued so we worked out way back to Route 1.

Kennebunkport, Maine

• Stay – Nonantum Resort
• Eat – The Boathouse
• Coffee – Dock Square Coffee House

Kennebunkport, ME to Saco, ME

12 miles
22 minutes

There are no coastal views on Highway 1 between Kennebunkport and Saco but it’s still a nice drive. Since it was too cool to stop at another beach – I had intended on stopping at Old Orchard Beach – instead we pulled off at the The Lobster Claw Pound & Restaurant in Saco, Maine.

This was a Boston to Bar Harbor road trip, so it’s only logical that lobster would be included at some point. Honestly, I didn’t think it would be a hot bowl of lobster bisque on a summer day, but with weather that felt more March than July, it hit the spot. It was so good; creamy with just the right amount of lobster meat in it.

The Lobster Claw has been in business, serving all things lobster for 50 years. In addition to lobster, they have other seafood and for the non seafood eaters, the serve steak, ribs and chicken.

Saco, Maine

• Stay – Atlantic Birches Inn (Old Orchard Beach)
• Eat – Run of the Mill Public House & Brewery or Quiero Cafe
• Coffee – Time & Tide Coffee

Saco, ME to Freeport, ME

33 miles
34 minutes

I’m sure there are plenty of perfectly good reasons to visit Freeport, Maine but for us, it was all about L.L. Bean. Founded in 1912, L.L. Bean is one of the oldest makers of outdoor shoes, clothing and equipment. If you’ve purchased anything from them, you know their products are good and last forever.

The official name of the flagship store in Freeport is L.L. Bean Discovery Park because it’s more than a store to shop in. It’s actually an entire complex of different stores from the L.L. Bean line up. It has an amphitheater for live music and other events and an area for kids to run around in.

Once we were inside the store, our hearts beat a little faster just seeing the rows of Bean boots and the classic L.L.Bean canvas bags. And the backpacks! What kind of backpack are you looking for? It doesn’t matter, they have it. In addition to the clothing and outdoor store there’s a separate store for L.L. Bean Home. Besides all this, if you are sticking around Freeport for awhile, there are tons of activities you can sign up for.

Maybe one of the most interesting things about the L.L. Bean flagship store, is that they are open 24 hours a day, 365 days a year. If you are wondering who shops at L.L. Bean in the middle of the night, I found this NPR article about just that.

Freeport, Maine

• Stay – Kendall Tavern Inn
• Eat – Jameson Tavern
• Coffee- Isabella’s Cafe & Bakery

Freeport, ME to Bar Harbor, ME

158 miles
2 hours 40 minutes

The final leg of our Boston to Bar Harbor road trip wasn’t too exciting. I would have loved to continue on Hwy 1 and visit places such as Camden and Belfast but it continued to rain the entire time. With the prospect of having to set up our tent in the dark, which I try to avoid, we got back on I-95 for the last 165 miles of the journey.

As it turns out, we did set up the tent in the dark but the good news was that as soon as we got to Mount Desert Island, where Bar Harbor and Acadia National Park are located, the rain stopped. So at least, we didn’t have to set up in the rain too.

To be continued……

More Boston to Bar Harbor Road Trip Tips

All of the places I mention in this article are places we actually stopped and visited. The suggestions of where to stay, eat and have coffee, have been carefully curated by me and are places – based on my research of the area – that I would stop when I have the chance to drive this route again. Some other tips:

• Part of Interstate 95 on this route is a toll road so plan accordingly.
• Gas stations were plentiful and we had no problem finding fuel along the way.
• If you fly into the area like we did, many of the convenience stores along Highway 1 have groceries, coolers and ice. Or you could always pack a soft-sided cooler in your checked bag or carry a backpack cooler. An insulated bag can double as a carry-on when you are flying and then use it to keep things cold on the road trip.
• Make time to stop at one – or several – of the many ice cream shops along the way. Highway 1 has so many. We wanted to try them all.

How Many Days do I Need For a Boston to Bar Harbor Road Trip?

• This road trip is a great one day trip but would be even better over the course of two days or even three.
• Since this road trip was more about smaller town, you probably noticed we totally skipped Portland. Even though we didn’t visit this time, I think it would be a great place to overnight if you are breaking up the drive. I love this hotel and this one.
• Kennebunkport – and Freeport north to around Brunswick – are also good overnight choices.

Road Trip Themes

This Boston and Bar Harbor road trip is the perfect area for a themed road trip. Here’s a few ideas.

• There are plenty of breweries and brewpubs in the area, so how about a brewery themed road trip (with a designated driver of course). Just around Kittery, there are six breweries. Blaze Brewing at Old Orchard Beach and the breweries around Kennebunkport would make good stops as well. And don’t forget to include Maine Beer Company in Freeport.
• Another perfect idea for a themed road trip is visiting lighthouses. I count about about ten on this route.
• There are also plenty of state parks that could be added to this itinerary. One that stood out to me is Wolf’s Neck Woods State Park near Freeport. Since parks and camping have been affected by the pandemic, check the website for up to date info before you make plans.

Road Trip Packing List

Here’s a few items that you might find useful on your road trip.

• Even in the summer it’s smart to pack a rain jacket just in case. This is one of my favorites.
• Most airports and parks have refillable water stations. You can carry your own refillable water bottle to make sure you always have water on you. Hydro Flask makes some of the best ones.
• Good earbuds are a must for a road trip.
• This is the crossbody bag – that doubles as a small camera bag – I carry everywhere, on every trip with me.
• A good trail pack or fanny pack is a must for hands-free adventures.
• Lastly, I may or may not be obsessed with duffle bags. They work so well for road trips. I have an older style REI bag that’s been everywhere. They don’t sell the same one anymore but their duffle bags are so well made and very affordable. Here’s a small and large version.

More Resources

• Check on flights and rental cars on Expedia.com.
• Look for more hotel and accommodations at Booking.com.
• Check trip reviews at Tripadvisor.
• And don’t forget trip insurance and roadside assistance

pin my boston to bar harbor itinerary here