
We ended 2021 with a trip out East to Massachusetts and Maine in November. It was our first time traveling to the East Coast together and the first time for each of us to travel to Maine. The purpose of the trip was to visit Maddix at his college prep school, Bridgton Academy, and see his last home football game. What I didn’t expect, was for the Fall colors to still be so absolutely beautiful! We definitely had a late Fall this year, and the weather out East was nothing short of perfect!
We flew into Boston, which is a quick & cheap flight from Indianapolis. We stayed at the Residence Inn just outside of Boston in Watertown, MA. It was an all-suite hotel, a perfect location, across from Arsenal Yards and the Charles River where Boston meets Cambridge.
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When we flew into Boston on Friday night, we decided to get tickets to the Celtics game and check out the Garden since neither of us have ever been. It’s a classic NBA arena that has been on my bucket list for a very long time. We waited until right when the game started to buy tickets, so we ended up scoring a really good deal. We had a blast at the game and I even got on the big screen!

In Boston we enjoyed great food and drinks at a variety of spots, all of which I would recommend:
Banners Kitchen & Tap- located in the heart of Boston sports, right next to the TD Garden. It was perfect for an appetizer and drinks after the Celtics game.
Tavern in the Square Allston- This spot was also within walking distance of the Garden. They had an amazing vegetarian menu and we ordered some late night food to take back to the hotel. Their Bang Bang Broccoli and Buffalo Cauliflower were delicious.
Russell House Tavern – This was a cozy, chic spot in the heart of Cambridge, Havard’s campus. We had dinner here with D’s cousin and I had a great Vegan bowl and one of the best cocktails I have ever had. It was Rose Gin, Moroccan Mint Tea, Lime an Angostura. Very memorable!
Gustazo Cuban Restaurant and Cafe- I wish we had time to eat at this spot again. There was an entire section of the menu dedicated to vegaetarian small plates and I also found some Vegan options too! The atmosphere was very fun and the wine was also top notch. This was my favorite restaurant of the trip!
Yvonne’s Boston– This was definitely my favorite spot! It is a very beautiful and fun supper club hidden away and decorated with gorgeous marble and mahogany wood. They had a tea set of cocktails on their menu and it was just so different and the vibe was exactly what we were looking for. I wish Indy had more spots like this!
The Bell in Hand Tavern – the oldest bar in Boston. It’s been around since 1795 and a very famous must-see spot in Boston!
Durty Nelly’s – a very cozy, friendly, Irish pub. A total dive bar!
Boston Nightlife
We rented a car and did a road trip on Saturday from Massachusetts, through New Hampshire up to Maine. We wanted to see Maddix’s college campus. After a quick visit to the football field and around campus, we drove another hour back to Portland Maine. Portland was exactly like I pictured it! The Old Port waterfront has working fishing wharves and restaurants and shops. It was beautiful! We went to lunch at DiMillo’s on the Water. It is a very popular restaurant in the marina in a huge former car ferry. It sits right on the water with stunning views. While it is a seafood restaurant, they were accommodating to me and gave me a salad and pasta. It seemed like a classic Portland restaurant. I wish we had more time to spend in Portland to really explore their food scene as well as the scenic views. Next time!
Portland
After our day in Maine we drove back to Boston and enjoyed dinner and drinks in the city with D’s cousin again. Sunday was game day and we traveled to Framingham, Massachusetts to watch Maddix’s football game. He had an excellent last game and it was an absolutely beautiful Fall day.
New England Trip November 2021 Recap Video:
I hadn’t been out East in years and I was reminded how much I love it out there. I really want to make it a priority to take my daughters back next time! It was so beautiful with all the fall leaf foliage. November seemed to be the perfect time to travel to the East Coast!