Before the fall weather blows in after a pretty hectic summer I wanted to spend time with my mother. So we took our favorite Boston to Maine roadtrip. I flew into Boston to meet my mom for our escape to Maine. We have traveled to Maine several times over the years since I was a kid. While I was more of a “city person”, I always found Maine so “down to earth”.No massive cities, but more quaint towns and villages, tasty food, and nature with its great rugged shore and outdoors.

I loved visiting places like Kennebunkport, Kennebunk, Bar Harbor, and Mount Desert Island / Acadia National Park and thought what better place could we go before the final days of summer pass us by than a road trip from Boston to Bar Harbor one of the best Maine road trips. Whether you just have a long weekend or a week it is the perfect escape in fall or summer to enjoy vacationland aka Maine.

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Maine Road Trip Part 1 Kennebunkport/Kennebunk Maine

First, we planned to spend a few nights in the Kennebunkport area and we had the chance to experience a fantastic glamping spot called Sandy Pines Campground .  After checking in and seeing their cute store, we went to our glamping tent that was air-conditioned. There are various sections of the park, but we had an adult-only area that made it quite peaceful. The entire park had that 1950s colorful vibe with its beautiful camper and red station wagon parked at the entrance plus the lovely colorful pool area.

If you’re not a long-time camper, these glamping tents and A-frames may give you a way to experience it at a higher comfortable level. After checking in we had to grab a bite to eat so we headed to a seasonal favorite Cape Pier Chowder House in Cape Porpoise to try their fish and chips and chowder. It was great enjoying their tasty dishes sitting on the waterfront under their tented porch. Loved it so much and it brought back past summer trips to New England.

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Cape Porpoise- A Hidden Gem on a Boston to Maine Roadtrip

Next, we were on our way to see historic downtown Kennebunkport, but first, we came across the little village called Cape Porpoise. As we drove we saw this coffee/food store called Cape Porpoise Kitchen that had also precooked meals and pastries, etc. There were limited seats indoors so we decided on a snack and we shared a great pressed chicken pesto panini before dinner and I had a coffee. It was so tasty and it was a quieter area I got to talk with a few locals who shared their suggestions on must-visit local spots.

Then it was time to head to historic downtown Kennebunkport and its neighboring Kennebunk connected by a bridge. This is a must when you visit Maine. Kennebunkport has been home to Presidents 41 and 43 with the giant Bush compound. It is so easy to walk around and explore the historic centers of Kennebunk and Kennebunkport since both are connected by a bridge. We walked around to see the shops, had BlueBerry ice cream and more coffee at H B Provisions, the General Store that had some veggies, and fruits, and bought a few bananas, etc. This was perfect for stocking up on things for our glamping tent and gave us time to enjoy the pool.


When in Maine have chowder and fish and chips! Literally the freshest I have had. I loved eating at Cape Porpoise Chowder House and the views from this restaurant that has been serving since 1956. This spot is located 10 minutes away from Downtown Kennebunkport. #visitmaine #mainefoodie #mainefood #seafood #newenglandtiktok #roadtripusa #kennebunkportmaine @TravelsofSarahFay-Solo Travel

♬ original sound – TravelsofSarahFay-Solo Travel

Grab breakfast in Kennebunkport

As we headed back to Glamp, we stopped at Bradbury Brothers Market at in Cape Porpoise to grab sandwiches for dinner. These subs were loaded and perfect for a takeaway lowkey dinner. Not only that they have delicious pastries like the largest Whoopie Pies that I ever saw. Besides Blueberry Pie, Blueberry Ice Cream, and Lobster, you’ll see a lot of Whoopie Pies in Maine. I never tried these although my mother loves them, so when I said that, the man there bought me one to try. The people were so friendly and it was fantastic and we split it since it was so big. 

The next morning we headed into town for breakfast at Mornings in Paris just over the bridge in Kennebunk. I loved the savory turkey and brie crepes and the morning breakfast sandwich; the coffee and espresso here were great too. 

Boston to Maine Roadtrips best food spots Mornings in Paris cafe for awesome crepes and coffee.

Want to learn about Kennebunkport take a walking tour through the town center.

Sarah Fay in Kennebunkport Maine a must visit destination on any Boston to Maine Roadtrip

Enjoy the best beaches in Kennenunkport

If you don’t think Maine has beaches with clear blue water, you have not been to Goose Rocks Beach. This is one of the best beaches in Maine and needs to be on your road trip from Boston to Maine. There is another general store called Goose Rocks Beach General Store and Morning in Paris located inside great to grab an iced drink to walk with along the beach. While there was limited parking near this path to the beach, further down the road there was another spot with more parking and very clear water.

It was so unique since you can walk out quite far during low tide, so it was very interesting compared to what I experienced in Florida. We were lucky to have great weather. After this, we went to dinner at the famous The Clam Shack on the bridge back in town. This is a famous walk-up stand that has outside tables to enjoy the area and we watched the sunset over the bridge while we ate, their world-famous Lobster Roll. What a great day and relaxing night to prepare for the final day in the area before going to Bar Harbor.

Best Coffee in Kennebunkport

Before the next day’s adventure, we found Coffee Roasters of the Kennebunks  It was awesome, we met the owner and the coffee was so great, we went twice. They have a great little sitting area inside and outside and many types of coffee supplies and food. This was perfect right before exploring the coast and going on two adventures in Kennebunkport located close by. Besides all the great lattes, cappuccinos, and fancy drinks, they offer a $1 coffee choice that is great for folks like my mom who only “should” drink decaf coffee or just want the caffeine fix. Besides other tourists, many locals were here to drink their morning joe. 

Must Do Activities in Kennebunkport

Go whale watching!

On this final day at Kennebunkport, we also got to go on a phenomenal whale watching and lobster tours. The Whale Watching Tour with was unique since it had steel rib low riding boats so you have a 360 view to see the whales very up close. We saw dolphins two types of whales, and got up close and personal with the humpback whale. This tour is an adventure whale-watching tour and can get bumpy, but is way more personable because of the smaller size. However, if you are like my mom with back injuries and can’t sit for 5 hours I suggest the Lobster boat tour. 

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Take A Lobster Boat Tour 

The Lobster Boat Tour with Rugusa Lobster Tours, which was an adventure with lobster boat Captain Bob, where you learn about the lobster catching process and how they work to keep lobster fishing sustainable (this trip was catch and release, so no lobsters were hurt during filming–lol). You cannot come to Kennebunkport without seeing the history of lobstering on your Boston to Maine roadtrip.

Take a drive on the Ocean Ave of Kennebunkport 

The best thing to do in Maine is drive along the coastline and in Kennebunkport you cannot miss a drive on Ocean Avenue. One of the first places you will find is St. Ann’s Seaside Chapel this place has an outstanding view, and has a historic church. As we continued a bit further down we saw Walker’s Point to see the Bush family compound in Kennebunkport. It served as the summer home to both President Bush 41,43 and their families. 

Other things to do in Kennebunkport, Maine:

Food tour

Cape Porpoise Kayaking tour

Luxury Catamaran Sailing

Boston To Bar Harbor Road Trip Highlights

There are many places to stop in between Boston and Bar Harbor, however, if you only have four nights I recommend breaking it up two and two with Kennebunkport and Bar Harbor. 

After exploring Kennebunkport drive 3 hours to Bar Harbor Maine. We departed the Lobster Boat tour and the whale watching tour directly after to head to Bar Harbor. On the way, we had to stop at the Blueberry Hill Dairy Bar on Route 3 in Ellsworth for some great blueberry ice cream. It was great and affordable, but just know that it is cash only if you stop here. You’ll find that is the case for some of these seasonal businesses, etc. Maine is famous for its blueberries that are small and quite tasty and it’s the only state that commercially harvests blueberries. I know Maine Blueberry Pie was my grandfather’s favorite, it brings back memories when I take road trips up to Maine since it is something I have done with my mom quite a few times. 

Sarah fay standing on top of Cadillac mountain the most eastern area of the USA you can watch the sunrise. It is one of the highlights of any Boston to Maine Roadtrip

Bar Harbor and Acadia National Park 

Bar Harbor is the largest town on Mt. Desert Island. It is a unique place filled with rolling hills, amazing hikes, quintessential New England towns, beaches, and a dramatic coastline dotted with lobster restaurants, lighthouses, and reminders of bygone eras. Don’t miss it on your Boston to Maine roadtrip.

Where to stay in Bar Harbor, Maine?

The Salt Cottages 

As we reached Bar Harbor on Mt. Desert Island, it wasn’t long before we came to our next stop at Salt Cottages. It was stunning, overlooking Frenchman Bay. This stunning resort was completely refurbished in 2022, with great cottages, a great pool, hot tub, clubhouse, fire pits, game rooms, etc. It was nostalgic with a modern flair. We had some great Blueberry Soda when we checked in and had a great time there on our final two nights of the trip. We had a lovely one-bedroom unit and enjoyed the nightly marshmallow roast at night. It truly was a memorable stay and so close to Acadia National Park and Cadillac Mountain.

That night we ate at Geddy’s, a seafood restaurant on Main Street in downtown Bar Harbor. We had salmon and linguine/shrimp dishes, and both were great. We then went back to toast marshmallows at the fire pit and wanted to get rest for our 9 a.m. reservation to enter Cadillac Mountain at Acadia National Park the next day.

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Drive the Park Loop Road Acadia National Park

After a fun relaxing night, the next morning we went to Choco Latte Cafe for coffee and a quick bite to eat downtown Bar Harbor before going to Cadillac Mountain for our 9 a.m. reservation time. This is a newer process, requiring a reservation to go to the mountain since it was swamped with tourists in past years (although I miss the old process where you can go in at any time). Cadillac Mountain is popular for the sunrise, the first spot to see it each morning on the East Coast. Just make sure you make your reservations in advance since it fills up. You also have to stop before getting there at the entrance to the park so it was great that neither entrance had a long wait. Make reservations here.

Don’t Miss Stops on Park Loop Road

After seeing the fantastic views from the mountaintop, we went off to see the roaring coast at Thunder Hole and then to Sand Beach. We drove along the Park Loop Road and then made our final stop to the park at Jordan’s Pond to have the famous Popovers at Jordan Pond House Restaurant  We always loved having popovers and tea/coffee.

The last time we were, I hiked around the pond while my mother relaxed here, with its great view of the fields, ponds, mountains, etc. In past visits, I got to do so many hikes like the Beehive Loop and Precipice trails, and the Bass Harbor Light Station, which houses the 1858 lighthouse sitting on the seacoast with its rocky coast. There is so much more to see, this is why we were here to visit some of our old favorites. 

Check out my article on 13 Reasons Why You Should Visit Acadia National Park here.

After a full day at Acadia, we ate dinner at Mainly Meat BBQ on Rt.3 near the Salt Cottages and enjoyed the Pulled Pork Sandwich and I got the epic daily special with short rib, with a side of Mac N Cheese. It was awesome and there was a great little ice cream called Udder Heaven Ice Cream Retreat next door that looked popular, but we were full from our dinner and we also knew the next day would be filled with much more food since we were taking a food tour before returning to Massachusetts. Plus we had to go back for the nightly s’more party at the Salt Cottage. Exploring Mount Desert Island as well as Bar Harbor is the highlight of any Boston to Maine Roadtrip in my opinion.

How To Find The Best Restaurants in Bar Harbor

The next morning we had a good breakfast at Cafe This Way, a quirky breakfast and dinner spot. It was really enjoyable and the staff was great and so helpful and cheery. We of course had the Blueberry Pancakes and coffee, Delicious. Then we headed downtown to meet with the 3-hour Bar Harbor Food Tour with Maine Day Ventures 

With this tour we learned more about the area while tasting some great foods like lobster slider picnic from Independent Cafe, then crabcakes at Gayln’s a classy restaurant with a great art collection, then had an epic Italian sandwich at LUNCH, before heading to an olive oil tour and then final stop, ice cream. I don’t want to give away all their secrets, but you do stroll around town and walk quite a bit, and the guide was so knowledgeable. It was a great wrap-up before heading out of town and perfect even for us who have been there before.


Gere are 5 Maine foods you must try in Bar Harbor with Maine Day Ventures culinary walk check out @Maine Day Ventures ! #mainefood #mainefoodie #seafood #foodtour #barharbormainefall #foodietravel #foodblogger @TravelsofSarahFay-Solo Travel @TravelsofSarahFay-Solo Travel


Bar Harbor to Boston- The Final Leg of Our Boston to Maine Roadtrip

As we left town, we drove through Seal Harbor where Martha Stewart has a home, and then Northeast Harbor which has a historic inn, yachts, and cute old-fashioned downtown, before going off the island to head back to Massachusetts. We were a bit sad that the trip was coming to an end, but we were glad we had such great weather with sunny skies since it started to rain when we left “the island”. Mount Desert Island is so cute, made up of a few small villages like Bar Harbor being the heart of it for me. I came here after graduating from Dartmouth College and then came a few other times with my mother. Bar Harbor and Maine is a place that draws you back no matter the season. It is a place that should be on anyone’s USA travel bucket list of adventures. 

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Want to have long weekend escape this 4 day Boston to Maine roadtrip is perfect for a getaway with friends, solo, or for mother daughters

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