Massachusetts- Whales, Witches and Wayfaring

Our family is attempting to travel to all 50 states through creative road trips. We prefer to choose a route which may have several destination stops throughout the trip. This often results in spending a short amount of time in one city. We love to get the flavor of the place that we are visiting by experiencing dining experiences, seeing a well-known icon from that area or simply experiencing the understated charm of that particular area.

This post shares about our time in Massachusetts. We spent time whale watching, visiting Salem and exploring Boston.

This portion of the trip is part of a larger New England road trip. We arrived in Massachusetts from coastal Maine after flying into Vermont and exploring New Hampshire. You can read about Vermont and New Hampshire here and coastal Maine here.

Our first stop was Gloucester. We arrived in the evening and we were staying at the Rockport Inn and Suites. We had a fine stay here. Breakfast was great and it was a good location. After dropping our things off at the hotel, we grabbed some dinner. We chose to grab something at Stones Pub and Eatery. My husband enjoyed his bowl of clam chowder. After dinner, we relaxed in the hotel. We wanted to be rested for our next day.

The next day, we had breakfast at the hotel and then left for a whale-watching tour in Gloucester (pronounced Glos-ter.) We booked our tour through Cape Ann Whale Watching and had a great experience. We purchased our tickets at a discount on Groupon so here is your reminder to always check Groupon when traveling. It was so fun to see the whales. The crew is so familiar with the whales that they have names and descriptions of many of them. They were able to share what they knew of their stories. I would highly recommend Cape Ann Whale Watching. Keep in mind that it is quite chilly out on the water depending on the time of year that you go.

After finishing the whale watching tour, it was time to head towards Boston. We made a quick stop for wood-fired pizza for lunch at Bravo by the Sea. They had a lunch special which was perfect for our family. We were in Massachusetts in October so we decided to go to Salem to check out the festivities. October in Salem is definitely worth a stop. We got lucky being there during a weekday afternoon which resulted in it being less busy there. We took pictures in front of some of the iconic buildings from Hocus Pocus and learned about the history of the Salem Witch Trials. We also got some fun treats at Whimsy's Sweet Life. It was a fun October stop!

After touring Salem, we drove on into Boston. We drove around finding our hotel and were able to see Harvard. We stayed at the Homewood Suties by Hilton Boston/ Cambridge- Arlington. As we were arriving, we discovered that Homewood Suites have a "Welcome Home Reception" which offers drinks and light appetizers. We grabbed a bite to eat and went to relax in the hotel room. It had been a very full day.

The next day, we had breakfast at the hotel and then headed out to explore Boston. We followed the Boston Freedom Trail on our own. In retrospect, this is probably a great opportunity to do a walking tour, but we did feel that we were able to learn plenty about the history by exploring on our own. Our girls have National Parks Service Passports so we took those along so that we could get stamps from historic sites. It was really amazing to see all of the history in this one city. We toured Paul Revere's boyhood home.

Halfway through our day, we stopped to have lunch in the Little Italy area of Boston. There are many restaurants to choose from. We chose Isabella's Ristorante. It was delightful! We were hoping to try cannolis from Mike's Pastry as we heard that those were iconic. We never made it because the line was always too long. This proves that they must be worth a stop!

After lunch, we continued on our walk and made it all the way to the Boston National Historic Park to see the USS Constitution. We definitely got our steps in on this day! In fact, it was now getting later into the evening so we opted to take a Lyft back to the car as daylight would be dwindling by the time we made the long walk back.

We loved our day in Boston, but it was time to hit the road as our next hotel was in Newport, Rhode Island. That night, we stayed at the Howard Johnson by Wyndham Middletown Newport Area.

For other ideas- check out the activities below.