Spoiler alert – this wasn’t my first time to New England, I grew up 20 miles north of Boston but left after college in the 80’s. I had actually planned on going back after spending a few years in Colorado, but that never happened. While I grew up in MA and spent a lot of time in NH, Vermont, and Maine when I was young, it’s been years since I played tourist in those states, and I must say, I enjoyed it.

I flew into Boston a few days before my friends did, in order to visit some friends. Once all three of us were together, we headed north to Maine for a few days. We did stop in Salem, MA on the way to walk around and have lunch before our next stop in Ogunquit, ME. This is a tiny town on the ocean, and worth a stop. There are wonderful shops and restaurants and places to walk or sit by the ocean. Since we had just had lunch, we stopped for dessert at “Big Daddy’s” Ice Cream on Main Street – great flavors and just the snack that we needed before heading north again to Portland Maine for the evening.

After checking in to our hotel and wandering around the waterfront, we picked Luke’s restaurant for dinner. It was right on the water, and while it wasn’t that warm, being late September, it was really nice to have dinner outside by the ocean and watch the sun set, the moon rise, and the boat activity. If you like lobster, this is the state to have some – or a lot.

There are many ways to see the coastline in Maine, but I think we found a really fun way to be a part of it all by taking one of the three daily mailboat runs. This large boat makes multiple stops at small islands surrounding Portland and picks up and drops off packages and mail. On the way back, people can board the boat to head back to Portland. While it’s not a tourist trip, the Captain did make comments about each island we stopped at and added some fun history. The weather was overcast but not too cold or windy and for just $17 it was a great way to spend a few hours.

We stopped to visit a few lighthouses along the way – my favorite being the Portland Head Lighthouse, just south of the city. It rests on a rocky ledge and is quite dramatic and majestic. After our day in Portland, we headed north again for about 3 hours to Bar Harbor, Maine, and arrived in the dark. We spent 2 nights there soaking in the quaint town and of course, Acadia National Park.

We spent most of the day in the National Park. Once again, the day was overcast, but you could still see pretty far and enjoy the rocky coastline of Maine while listening to the roar of the ocean. We enjoyed a casual lunch by the ocean again and then had Italian for dinner. After breakfast on the following morning, we took the scenic road (slower but picturesque) to Conway NH which was about 4 hours. We stopped in Somesville and Seal Harbor to take photos, among other stops.

The reason we chose Conway NH was because it was close to the Kancamangus Highway, which was our first stop after breakfast the next day. Having grown up in MA, near the NH border, I spent a lot of time camping, hiking, and skiing in this area with my family. I have very fond memories of this stretch of highway, which is recognized as a National Scenic Byway and stretches from Lincoln to Conway over 35 miles. Since we were visiting in early October, we had hoped to see some Fall foliage, but due to a wet Spring, the leaves were just starting to turn, so we were a bit early – but it was still beautiful.

We were only in NH for an overnight and then we made our way to Boston to finish our last 4 days there. We stayed in Concord, MA instead of Boston, due to the high prices of hotels in the Fall. Since we had a rental car, we just drove to a parking lot associated with the MBTA subway system and for only $2 we took a train into the city each day and walked everywhere. One morning we got off in Cambridge and wandered around Harvard Square for a bit before heading into Boston, and another morning we started out at The Prudential Center’s new viewing area that had previously been called “Top of the Hub”. View Boston as it is now called, just opened in June of 2023 and offers spectacular views of the city as well as a wonderful restaurant and interactive exhibits – well worth a visit for sure and we hit it on a clear day 🙂

The Freedom Trail begins at the MA State House on Beacon Street at the top of Beacon Hill. This is adjacent to the Boston Common Gardens which was established in 1634. The trail is only 2.5 miles and the route is well-marked with outlined bricks to follow with 16 historically significant sites to see. There are many options for tours to take, but we chose to do it at our own pace, as everything is clearly marked along the way.

We split the Freedom Trail into two days because we added other things before and after each day, but it’s completely doable in a day. We chose not to visit Bunker Hill Monument as it was over 80 degrees that day and there was construction going on at the top of the monument, which is where you would climb the stairs to look out. We also did not visit the USS Constitution, which I have seen many times, but is well worth a visit. My one (ok, two) request was to have Pizza in the North End, the Italian section of the city, and then get Cannoli from Mike’s Pastry for dessert. I make this stop every time that I’m in Boston because I just can’t get enough Italian food and I haven’t found better Cannoli’s anywhere – they never disappoint – lol.

We ended our trip to New England in Concord and Lexington MA where much of this country’s history began. This area is a short drive (depending on traffic) from Boston and is steeped in history and gorgeous old architecture. We had our final meal in New England on the veranda of a beautiful old Inn in Lexington and it was a lovely way to finish out our little tour.

Visiting Massachusetts for me is always bittersweet – I’m from there, but I’ve been gone so long that I don’t feel connected anymore. But, this trip seemed different because I didn’t just visit my friends, I was immersed in the history that I love and that I miss. I hope to visit again soon and enjoy more of what Massachusetts and the rest of New England has to offer…