Adam and I traveled up to Boston, MA last October and it was one of the most fun trips I have ever been on. He’s been trying to get me up there for years (since I’m such an NYC girl) and I am so sad it took me this long to go. We went right in the middle of the month which is the perfect time for ideal weather and fall foliage. With fall just around the corner, I thought it would be a great time to share a little travel diary and trip recommendations. If you are looking for somewhere to get away to this fall, I would HIGHLY recommend New England.
We went over a long weekend and our trip basically consisted of three legs. The first leg was spent touring downtown Boston. The second leg was spent (on Friday the 13th!) touring around Salem, MA and yes, it looks JUST like the movies! The last day we spent driving through some of the oldest, most picturesque towns of the state and up through some adorable coastal towns (I will do another blog post in a few weeks with more detail on our MA state road trip!). It was packed full but like I said, it was one of my favorite trips and I would do it again in a heartbeat!
What We Did:
Downtown Boston – This was my first time to Boston so I definitely was out to get the full tourist experience. We landed early morning, checked into our hotel, and immediately headed out. Our first stop was Fenway Park! It’s such an iconic place and even though we didn’t go inside, it was so cool to see it and read all of the history about it. We made our way down Boylston St. on foot and of course stopped at the Boston Marathon Finish Line. The Boston Marathon is a world major on our bucket list so it was exciting to see where so many greats have ran through.
The Freedom Trail – This was a no brainer for us. Adam loves history and I love exploring cities on foot. The start of it is in Boston Commons. We went to the visitors center and paid for a map and proceeded on our self guided tour. It was such an exciting way to see so many things around Boston. I would read Adam the short stories from our map and he would just travel back in time.
Salem, MA – As a lifelong Hocus Pocus fan, I needed to go to Salem. Since it is such a short – and scenic – drive up the coast from Boston, it was a no brainer to go spend a day there. We were there on a Friday the 13th in October, so it was obviously a bit crowded but it didn’t seem to bother us. People were in costume and definitely in the full Halloween spirit. We got there early and walked around a good bit, we did a Salem Witch Trials history show,and spent the afternoon taking in all of the sites. I will say it is more spread out than you may think. There were a few things we would have liked to see but we would have had to drive and because of the crowd, we didn’t want to leave our parking spot. But, there was PLENTY to do within walking distance of the main downtown. The town website also puts out an event calendar for the month of October (I’m not sure if they do it throughout the year or not, too) and we had already picked a few things off of that to do and see.
Road Trip – After we left Salem, we headed inland a little bit to a small town called Sudbury to stay the night in a very old historic hotel, the Wayside Inn (which I talk more about below). We stayed one night and then continued on our journey where we headed southeast to begin a driving tour that I had planned for us. As you can tell from my other travel diaries, we have gotten to where we really like to rent a car for a day or so on trips and just spend some time driving around seeing things that we wouldn’t normally get to see. We took all back roads (no highways) and absolutely soaked up every moment of gorgeous Massachusetts. Before our trip, I looked up the best Massachusetts road trips from this website. I put a few together that worked for our timing and route and it was just a blast! I am going to do a full blog post in a few weeks about all of the fun stops we made along the way.
Where We Ate:
I will preface this with I LOVE seafood. And I reallyyyy love clam chowder. So it was a must that we go to seafood places when we’re on the coast.
Blackbird Doughnuts – I know Bostonians are totally Dunkin’ people, but I researched to find a well known gourmet donut shop. They have a couple locations in town but we went to the Fenway Park location, as it was right at the start of our plan to walk the city. Oh em gee they were good. I got an apple cider and a chocolate covered donut and a coffee and I could have eaten about a hundred more. They were delish and I highly recommend a stop at one of their locations.
Union Oyster House – Very famous, this place is known as the country’s oldest operating restaurant. It is right on the Freedom Trail path and about halfway through, so I knew it would be a perfect spot to stop and have lunch. We ordered some clam chowder, fresh oysters, and then I had a fish sandwich. I am literally not lying when I say I love seafood. We sat upstairs and the whole place is just filled with history. It was such a cool place and I the food did not disappoint.
Caramel Patisserie – Macaroons in Salem. This place needs no explanation!
Sea Level Oyster Bar – We ate lunch here while we were in Salem. When we travel, I do like to find places that take reservations so that I know we’re not wasting a lot of our site seeing time on waiting around for food. This place was on the water and the menu looked amazing, so I was all in. And boy was it good. We sat at the bar looking out over the harbor and stuffing our face with clam chowder covered fries and oysters.
Central Warf Company – Sitting right on the water, this was the perfect last night dinner spot for us. We sat out on the patio and took in the beautiful view. Again, ordered seafood *big surprise* but the food was great and the cocktails were a-plenty. I also thought it was priced pretty reasonably considering it’s menu and location.
Where We Stayed:
Embassy Suites at the Airport – So we stayed here for two reasons…we knew our trip was going to be broken up with one night here, one night in Sudbury, MA, and our last night here. So we really wanted to be close to the airport rental car places so that we didn’t have to waste time doing that and we also wanted to be close to the airport for our early morning flights. Im sure there are really great places to stay in downtown or other parts of Boston, but this location really worked for the whole of our trip and Embassy Suites are usually nice hotels. It’s an airport hotel so obviously it was close for our flights and rental cars, but it was not a bad commute to get anywhere we wanted to go downtown.
Wayside Inn in Sudbury, MA – After we departed Salem, we headed east. We wanted to stay in a picturesque historic Massachusetts place and stumbled across the Wayside Inn. It was an ideal location for what we wanted to do the following day after we were planning to check out, and Sudbury is the cutest town. Especially in the fall. The Inn was absolutely beautiful. It is the oldest operating inn in the United States. It sits on 125 acres that also house a chapel, a grist mill and an old barn among other historic landmarks. When we checked in, they handed us a KEY (not swipe card!) for room 6! (I know no one is used to this anymore!) The inn also has a restaurant that was packed! I think they had several bars too that were crowded. We checked in around 5pm and we were told the restaurant is one to rave about. Unfortunately, we did not get a chance to eat dinner or breakfast there but we heard great things. I had printed out a property map and we immediately went to explore the grounds. It was so beautiful. By night time, the restaurant cleared out and the inn quieted down. I’m not going to lie, it was a bit eerie to me but that was part of the fun! Overall, I would absolutely recommend staying a night or two here and I would do it again. I think next time I would roam around the grounds more and definitely try the restaurant!