5 Day Boston-Maine Road Trip

Boston-Maine Road Trip In 5 Days

We had what I would consider to be a quintessential family vacation last week. The secret sauce for our family trips seems to be a little city time followed by ocean/lake time with some type of athletic event sprinkled in. It worked well when we were in Portugal and was a success again with our trip out East. We recently spent 5 days in Boston and Maine. It was a whirlwind and not how we usually travel. Our family tends to settle in for at least a few days before moving on to the next setting. However, our list included several stops and we were determined to get to them all.

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Monday- Boston

Boston is a city rich in history, is walkable, and just has an overall wonderful feel to it. This wasn’t our first trip to Boston (read what to do with younger kids here) and it certainly won’t be our last.

We flew into Logan International Airport around 2:30pm, quickly checked in to our hotel, and grabbed a late lunch at High Street Place, which was close to our hotel. We all found something we liked from four different vendors- it was perfect!

Because it had been quite a while since our children had been to Boston, we decided to try to squeeze in a Duck Boat Tour (and basically ran across town to catch our boat). It was worth it! The boat tour was incredibly informative as well as highly entertaining. Despite a solid effort of attempting to avoid volunteering to drive the boat in the Charles River, both of our kids gave in to our tour guide and tried it.

After the duck tour, we joined the crowds walking toward Fenway Park, stopping in a souvenir shop to get our gear. Fenway Park was built in 1912 with subsequent renovations. It is the oldest Major League Baseball ballpark. It is old and quirky and absolutely wonderful. We were able to purchase tickets about a week before the game. (It likely helped that we went to a Monday game). Our seats were great and the ballpark gave very all-American summertime vibes.

Tuesday- Beacon Hill/Cambridge, MA & Portland, ME

The next morning, we grabbed a quick breakfast in Beacon Hill before stopping in Cambridge for a quick walk through Harvard. Then, we hit the road for our 2 hour car ride to Portland, Maine.

Portland is the largest city in Maine and is known for its marine culture, 19th century architecture, and, as of late, its food and drink scene. The brick streets and buildings are charming. There were enough big name stores scattered in with the cute boutiques to keep both our daughter and myself happy. R and our son were able to charter a fishing boat at the last minute. While I am not jealous of the fishing, I do feel that we missed out a bit on the beautiful views, including glimpses of Maine’s oldest lighthouse (1791).

As mentioned above, Portland is quickly gaining a reputation for its culinary scene. I had my heart set on a brown butter lobster roll from Eventide. Eventide is a James Beard award winner and also features oysters and shellfish. We only had about a 5 minute wait because we went at 3:30pm but if you eat at normal hours, you may want to plan to put your name in and then do some shopping or city exploring.

Wednesday- Bingham, ME

We woke up very early and drove 2 hours to Bingham for white water rafting with North Country Rivers Maine. We really liked this company and their focus on fun and safety. Unfortunately, it was cloudy and cold (for summer). Luckily, though, we had the option of wetsuits and splash jackets (although we all were then needing a definition of what a wet suit does exactly lol). We were also provided with water shoes, life jackets, and helmets. Our guide was engaging and informative. We signed up for the Kennebec River with includes Class 2-4 rapids (the ranking system is 1-6). We took a 30 minute bus ride to the starting point where we carried the raft down to the river. Most of rapids were in the morning followed by a nice float down the river in the afternoon. Our kids loved the rapids and wished that there were more of them in the afternoon. (Had it been a sunny, 90 degree day, I think they wouldn’t have minded the float as much.) I appreciated the rapids being spaced out with calmer waters. Our raft hit a rough patch of water and tipped up, dumping most of the rafters into the river. It was nice to have calm waters to catch them and get them back in the boat. (The company also does a good job of spacing out the rafts with other rafts always watching out for each other and helping out as necessary.) We then headed back to the cabins via a 20 minute bus ride to change and eat lunch together. After purchasing our photos, our family took off for the 2+ hour drive to Bar Harbor.

We settled in to our hotel room, walked to dinner downtown, and then called it a night.

Thursday- Bar Harbor, ME

We stayed at the Harborside Hotel, Spa, and Marina and I would highly recommend this property. It’s location is amazing for so many reasons. We were a 5 minute drive from Acadia National Park, could walk downtown to eat in less than 3 minutes, and we were right on the land bridge out to an island at low tide (which also made for excellent crab hunting). The service was impeccable with easy texting for requests, free parking, access to the pool/hot tub/clay tennis courts/etc. next door at the Harbor Club, and free coffee in the room and also to-go in the restaurant (you know this is of major importance to R and me). Oh, and there was free laundry, which feels soooooo nice after a week of travel and dirty clothes gathering.

But back to Thursday. We drove to Acadia National Park around 10:30 am. (It was semi-tempting to try to see the sunrise at Cadillac Mountain but felt risky with the cloudy/foggy weather.) This was all 4 of our first time visiting a National Park. I purchased a pass online and the hotel printed it for me. We found parking at the main entrance and hopped on a bus for Beehive Trail. This trail was amazing! It was very rocky and, at times, we had to use metal rungs to climb up the side of the mountain. The hike was challenging enough to keep all of our attention and focus. The views were breathtaking!

Acadia National Park- Beehive Trail — Note: I’m not typically a backwards hat type of girl- but our son didn’t want to wear his hat about halfway up and, as usual, I got the rejected items (even without my big purse in which to stash them).

On our way back down the hill, we somehow joined the Bowl Path and ended up where we started at the beginning of the Beehive Trail. (I would recommend purchasing a Park Map- we did not and our Apple Maps were spotty in the park. We were able to manage by following other people and using a less detailed map from the newspaper provided on the bus.)

We walked up the road to catch the bus by Sand Beach. Sand Beach is a “must see” in my beach-loving brain. The ocean mist and fog combined with the dappled sunshine made it feel like a dream. Had we more time, I would have loved to hike the Ocean Path. (Apparently, we did not prepare our children well. They assumed the we were doing one hike and then hitting the hotel pool. In my mind, we were going to be hiking all day.)

We were able to squeeze in Jordan Pond with the promise of lunch and popovers. The water was once again beautiful and we could have hiked around the lake, but Beehive sort of wore everyone out. We took our last bus ride back to the car and headed to the hotel.

At the hotel, we noticed people walking across an exposed land bridge to Bar Island. Our son and I headed out but quickly became distracted by looking for crabs. This land bridge becomes walkable to Bar Island during low tide and is then completely covered during high tide. It is a really neat thing to witness!

After some more pool time, we went into town for our final dinner and some ice cream. Bar Harbor is such a cute town right on the water. We purchased our souvenirs and then wandered back to the hotel to pack.

Friday- Bar Harbor, Freeport, Boston

Our flight out of Boston was not until 7:30pm so we were able to have a leisurely morning and take one last hike out to water views. On our way back into the city, we stopped in Freeport to see the L.L. Bean Flagship Store and get lunch.

Somewhere in New Hampshire, we got a text that our flight was cancelled. We rebooked a different flight for the next morning and got a hotel in Boston.

We checked into The Dagny. I couldn’t stop taking photos of the glamorous and playful Art Deco design, which is a nod to the fact that the hotel’s address once was home to Boston’s first Art Deco Skyscraper.

Because it was late and we all needed dinner, we decided to head to the North End to see what our options were. (Bonus that we came across Paul Revere’s house.) It turns out that there were many, many choices, mainly of the Italian food variety. The North End was hopping on a Friday night. We thought we might get something sweet at the famous Mike’s Pastry, but the line was too long (even late at night!). Next time.