A New England Road Trip: Boston, the White Mountains, Grafton Notch, and Portland

Back in June of 2016, my best friend Ashlee and I took a road trip up to Massachusetts, New Hampshire, and Maine. We left on a Thursday afternoon and came back on a Monday. We had planned some specific things we wanted to do ahead of time but also left space for us to do add things in that we came across. Below is as much of our itinerary that I can piece together from memory and photos.

Thursday – We left in the afternoon and got into a hotel outside of Boston around 8 PM ish. We were exhausted. The hotel had warm cookies at arrival which we quickly consumed and then went to bed.

Friday – We spent the whole day wandering Boston and walked about 15 miles from sunup to sundown. It was tiring, but so fun.

Since we were staying outside Malden Center, we took the T rail from Malden into the city so we didn’t have to park any cars.

After getting downtown, we stopped for coffee at Cafe Nero which has the most beautiful aesthetic.

Next up was the Boston Public Garden. We road on a swan boat and explored the park. It’s right next to Boston Common and Beacon Hill which we explored next with its historical homes and little shops before heading to do fun nerdy history things.

When I was younger and went to Boston with my parents, we walked the Freedom Trail. It has the famous stops in Boston on it’s path and is designated by an actual trail in the sidewalk. Ashlee and I decided to go on follow the trail and stopped at Boston Common, the Massachusetts State House, Old North Church, the Paul Revere House, the site of the Boston Massacre, as well as a few other stops.

Our walk was quite a few miles out and back, so by the time we finished we were hungry. We ate at a little Italian place near the Paul Revere house before heading across the bridge to the Lawn on D.

When leaving the Lawn on D, we had to head back to find a T station that would take us to the orange line and back to our stop. It was quite dark when we left, so at times, it was also a little unnerving. We didn’t know exactly where we were and we were in an area that seemed like an abandoned warehouse district. We found our way to the T station, with only slightly elevated heart rates from wandering through the city in the dark.

We went back to our hotel and rested up because the next day would be one that would include quite a few hours of driving on our way to Maine.

Saturday – Our plan for the day was to head up toward Freeport, Maine. We initially were going to travel up the coast, but decided to detour through the White Mountains in New Hampshire. On the way, we saw a sign for Loon Mountain Resort that had outdoor adventures, so we got off on the exit and headed toward the mountain resort.

They had options for a gondola, zip lining, hiking, and rock cave mazes, so we decided to do them all. We took the gondola to the top of the mountain, found the rock cave maze and squeezed ourselves through these small little crevices between enormous boulders. We hiked up to this wooden tower and then went zip lining across a creek. It was one of the best detours I’ve ever taken.

Our next stop was Grafton Notch State Park in Maine. We parked near the Appalachian Trail crossing and hiked the Table Rock Loop trail. It was steep but the views at the top were beautiful. While researching this post, I found pictures of the top of Table Rock during the fall, and wow. It looks incredible when the leaves are changing. Apparently I found a walking stick during our hike, which is highlighted in the bottom picture of the gallery below. Who knew?

We didn’t have service out where we were and my phone didn’t really work in general so we relied on screen shots of maps or turning on the GPS every so often to navigate our way through the mountains. It seems crazy, but this was only 4 years ago and the GPS abilities we had on our phones at the time was subpar. We headed toward our lodging for the night (Super 8) and on the way stopped by waterfalls, a stand to get pies, and then to a brewery in the area for dinner.

We stayed at some budget Motel 8 for the night where the bedding or walls, or both was lime green. I don’t have photos, which means it wasn’t cute. But it was affordable.

Sunday – We began to navigate our way down the coast of Maine on Sunday from Freeport to Portland. We stopped at L.L Bean on the way and then had lobster rolls and donuts for lunch in Portland.

We checked into our hotel (I don’t even know where) and then went to get dinner on the water from the Lobster Shack with picnic tables outside. It was delicious and an incredible view and affordable. We had a great time watching the sunset during dinner.

After dinner, we found ourselves at some country bar in Portland. The options for seating included porch swings, oversized stools shaped like farmer bottoms, and tractor seats. I remember that every table had outlets for charging which we thought was genius at the time. The drinks were great and the atmosphere was fun.

Monday – We drove the 8 hours or so back to Lancaster County. I don’t really remember any of it, and I have 0 pictures so we must have just drove straight back with no fun detours on the way.

Looking back on this trip, if I were to head up to these areas again, I likely would have spent more time exploring the area around the White Mountains and Grafton Notch. They have a other gondolas and cog railways in the area as well as scenic roads to the top of mountains. Since those are all my favorite things to do on trips, I would add these to my itinerary for next time. Oh, and also I’d add more lobster rolls because they are so YUM!