New England Weekend Road Trip | Boston, Connecticut, and Rhode Island
My friends and I usually try to go to some far away place for our reunions. We’ve been to Iceland and the Azores – both islands in the Atlantic Ocean. Well, this year we decided to stay domestic. We decided to visit our friend in her neck of the woods on a New England road trip.
As you may know, it’s easier to fly into larger airports. After a lot of digging, it turns out Boston was the cheapest airport, and it was only an hour and a half from her hometown. So, since I had never been to Boston, we ended up with the perfect itinerary. We would be seeing Boston, a little bit of Connecticut, and a quick pit stop in Rhode Island.
Warning, our itinerary was a little rocky starting out as Boston was tough to navigate, especially in Friday night traffic. While we didn’t do much Friday afternoon, we had a lot of fun Friday night and Saturday morning so keep reading!
FRIDAY
To begin, we each headed from our respectful cities to Boston Logan International Airport. I flew in from Nashville, my other friend flew in from Rochester, and my other friend drove in from Manchester, Connecticut. She picked us up from the airport, and we ran into each others’ arms. Needless to say, it was exactly like you see in the movies.
It was afternoon, and we immediately made our way into the city of Boston. Yes, the city is as dreamy as you see in the movies. It’s historical yet modern, and people were walking around the streets in the cold, brisk air. I was trying to navigate while also take in a new city I had never been to. Then, we parked in a parking garage and headed out to walk.
Tip: just get out and walk around as much as possible instead of driving the busy streets!
STOP 1: Quincy Market/Faneuil Hall
First, we walked maybe a block to Quincy Market. This is a massive food hall packed to the brim with different food vendors. There is any type of food you can imagine, and everyone wants you to try theirs. There are some spots for sitting or with tables to eat. Also, you can just walk around and take in the sights and smells.
We walked down the long straight line and looked at every single option. Even after that, we still couldn’t decide what we wanted to eat. Finally, our local-ish friend told us about the restaurant “Cheers.” It was located a little off to the side from the other stalls, but it was a nice dining area with bright light shining in from all the windows.
My friend and I who weren’t from this area had never heard of it before. I’m sad we didn’t, because it was delicious! I got the Fenway Special, because Boston, right?
It was two hot dogs and I added chili and cheese to make it the real deal, as well as French fries on the side. It was a lot of food, but I was in heaven. The restaurant even gave us “The Cheers Trail,” which guides you from one Cheers to the next. It would be a great DIY walking tour, because it even has most of the Freedom Trail sights along the way.
STOP 2: Admire the Architecture
Next, we decided to just walk around the city and take in what we could. It was pretty freezing, so we honestly didn’t have the energy to explore much! We were able to take in the sweeping skyscrapers and admire the architecture. Each street was similar yet had its own twist in this area near Quincy Market in what is the “Financial District.”
While we wanted to stay, we decided to hop in the car and do more of a driving tour.
STOP 3: Boston Harbor Walk
Next, we drove to what is called the “Boston Harbor Walk” on Google Maps. While it took us to more of an industrial sidewalk, we still were able to get views of the Boston Harbor and watch the sun start to set over the Boston skyline.
On the drive there, we also drove past the Boston Tea Party Ships and Museum. This was really funny, and if you have ever gone, I want to see pictures! I don’t even know how you get to it.
All in all, I would recommend spending that time finding a beach or the real Boston Harbor Walk to explore. It’s a fun way to see the city from the outside looking in, and would be a beautiful spot to watch the sunset.
STOP 4: Hotel Boston
We were freezing at this point, so we went to check into our hotel for the night. As you can imagine, hotels in Boston are pretty expensive – especially on a Friday night! We ended up booking our hotel a ways outside of the downtown area, but it ended up being perfect. Driving there, we were able to see more neighborhoods in Boston, and it started to look like those picturesque townhome streets with the beautiful stoops out front.
It was a decent hotel, and of course, if it offers complimentary breakfast, count me in. We checked in, brought our stuff in, then took a nap. The cold air had definitely worn us out. We decided that it would be fun to go out for a fun dinner and drinks, and then we ended up staying out for more drinks.
Hotel Boston is in the Boston College area. We were looking around the area on our maps, and there were a good amount of bars and restaurants only about a 7 minute Uber ride from the hotel.
STOP 5: Cityside Tavern
First, we went to Cityside Tavern. They had a good menu, and a fun-looking atmosphere. Perfect for what we wanted. We wanted to be able to talk, but also have good drink options and relax together.
We ordered the guacamole and chips and also the buffalo dip with chips. So here we were, sitting with two massive trays of chips and dips – I couldn’t be happier.
Then we ordered multiple drinks, but the best part was that they had specials where you could order a shot and a beer or a shot and a seltzer, etc. They had an extensive drink menu, and there really was something for everybody.
STOP 6: Mary Ann’s
RIP. According to Google, this spot is permanently closed, but I still have to give it a shout out. Dive bars are amazing. If you haven’t been to one, go as soon as possible. They are cheap, typically quiet, and very local. It’s what makes them so unique and special. My friends and I met working at a summer camp in a very small town in Wisconsin. This meant it only had dive bars, so that was our vibe.
When we saw Mary Ann’s on our Google search, we just had to go. We couldn’t even find it at first. There was no sign and the entrance looked just like a random building on the road and the door was hard to even open. Finally, we decided to just go for it, and then we were inside. And, we were literally the only people in the bar. It was perfect.
We spent that night hanging out with the bartenders and loving our cheap beers. Eventually, a bunch of college students started coming in, but we just got to people watch from the bar until we were ready to crash. We will miss you, Mary Ann’s – the most authentic experience in Boston.
SATURDAY
We woke up Saturday morning and made our way to the complimentary breakfast at the hotel. We had planned to spend Saturday morning in Boston to see the rest of the sights we had missed Friday night. After that, we were heading to Connecticut to see more of my friend’s hometown.
STOP 1: Fenway Park
We weren’t able to actually go in, because it was closed, but we walked around the entire park, admiring the statues and reading the signs. Everything around it was Fenway-themed, and I would love to go to a game there some day. It seemed like a place where people really came together and bonded over their love for Boston.
STOP 2: Boston Common/Boston Public Garden
Next, we went to this big green space in the middle of the city. I love going to parks in giant cities, because it reminds you that it’s not all concrete and there’s still nature and outdoor fun to be had. We simply parked on the street really close to it and payed for the meter, which was really cheap. Warning: we tried to see the famous Acorn Street in Beacon Hill to get some pictures, but there were signs up saying you need a photography permit!
These two parks are across the street from each other. There were people having a dog club meet up of some sort. There were people ice skating. Also, there were people waiting in a massive line for a Bernie Sanders rally. So many people were gathering in the park with friends, family, or alone – even on a brisk morning.
STOP 3: Harvard
Of course, we had to stop by and see Harvard. While we didn’t go in any of the campus buildings, we walked around the grounds and admired the historic nature of the campus with the students strolling around their home. On a Saturday morning, the campus was packed with tourists like us just wanting to see the famous university.
The archways in between buildings, the massive staircase leading up to the library, and the hidden alleyways make this campus unique and special. We even got to see the boathouse where the rowers go out onto the river.
When we were done walking around, we stopped in at the bookstore nearby, but it was mostly actual textbooks for the students, but you can find some Harvard gear there as well if you want!
STOP 4: Shady Glen Restaurant & Ice Cream Parlor – Manchester, CT
After Harvard, we left Boston and started the hour and a half drive to Manchester, Connecticut where my friend lives. Obviously, we had to stop at a gas station for a quick snack, and it was different than any I had seen before. There was a food court inside?!
Anyway, it was really cool, and it helped me realize that New England was truly different from being in the South. Even the architecture of the homes that we drove past just looked older, more colonial. I loved staring out the window taking in the new environment.
When we made it close to her hometown, we were all very ready for lunch, and she took us to her favorite spot. It is extremely local, and it looks like something out of an old diner movie. Shady Glen Restaurant and Ice Cream Parlor has a simple, yet decent-sized menu. They are famous for both their milkshakes and their fried cheese. Yes, I said fried cheese.
My meal consisted of a cheeseburger with fried cheese on it, French fries, a side of fried cheese, and a giant milkshake. The milkshakes even come with the silver metal mixing cup so you can keep refilling your cup as you go. I definitely couldn’t finish this meal, but it was such a fun experience. The entire restaurant is filled with locals.
Also, all the tables are connected with a big open area in the middle so the waitresses can walk through to take orders and deliver food. Such an authentic restaurant, and it has been around for so long without any changes!
STOP 5: Urban Lodge Brewing Co.
After literally being so full, we couldn’t do anything but lay down at my friend’s house and watch crime shows. Eventually, we got ourselves up, bundled up, and headed out to find that it was snowing a little bit! My first New England snow experience. Apparently, the thing to do in Manchester is to go to breweries, and they have SO many!
Each of the breweries are really unique, and we went to the first one of the day – Urban Lodge Brewing Co. This looked like a ski lodge from the outside, with wood paneling, and it even had an outdoor sitting area to hang out around fire pits and stay warm.
Inside, there were games, like corn hole, all throughout the first room. When you go to the bar to get your beer, it’s located inside of what looks like a living room inside of a cozy cabin.
When you get beer, me and my friend who were visiting each got flights of beer. I recommend you do this too, that way you can try lots of their craft beers and see which ones you like! We played corn hole, drank our beer, and then headed to the next brewery.
STOP 6: Connecticut Valley Brewing Company
Next up, we have the Connecticut Valley Brewing Company. I love these breweries because they each had something to actually do while you’re there. This one has just a big open room with a lot of high top tables. Each table had different games like Sorry or even just a deck of cards.
We each got a delicious craft beer from the bar on the far end of the room and then sat and played cards for a good while, getting too competitive. It was so nice to have a beer to warm you up on a cool night in New England February.
STOP 7: Boneheads Wing Bar – Rhode Island
My friend who was the local swore by this wing place, and it was in Rhode Island. I had never been to Rhode Island, and we are all always up for an adventure, so we were on our way in the late evening to Boneheads Wing Bar.
I understand the hype. Not only do they have a large beer menu, they also have any kind of sauce for wings that you can imagine – even some you don’t want to imagine. They have anything from Peanut Butter and Jelly to Mac and Cheese Dry Rub.
They have all the classics, including buffalo to barbecue. Not only typical sauce flavors, but they also have s’mores or syrup flavors. They have everything, so why not go for it and try something new while you’re there!
SUNDAY
STOP 1: Cosmic Omelet – Manchester, CT
After a long drive back that night full as can be on fried pickles and wings, we crashed and only woke up early because we had to get a start to our day! We were going to Cosmic Omelet, in Manchester, CT, again – in my friend’s hometown. This food was incredible. I don’t know how I was able to eat all of the amazing food I did on this trip in such a short amount of time.
Anyway, this place is obviously famous for their omelets. But, their omelets are different. The amount of combinations of foods you can put in their omelets is honestly amazing. There’s something for everyone. And, they have loaded hash browns – with cheese, bacon, and even ranch. The whole restaurant has fun art on the walls and the floors, and even the menus are designed to match.
I got “The Big Buckin Chicken” omelet, which basically has chicken tenders, BBQ sauce, bacon, and cheese. That, with the loaded hash browns plus toast that comes with it is plenty of food.
Other omelets have any type of meat you could want, any cheese you could want, any sauce you could want, or even different vegetables. The options are endless, and when in doubt, you can make your own. They call it “cosmic,” because you can add cream cheese to any omelet to make it “cosmic” – truly a New England restaurant.
STOP 2: Henry Park – Vernon, CT
Before we had to head back to the airport, our friend showed us her childhood hang out spot in Vernon, Connecticut, which was Henry Park. The park had different recreation areas, but the biggest attraction was at the very top of a hill. In the park, there is a giant tower that sits atop a hill and gives expansive views over this area of Connecticut.
My friend said she used to go there often to listen to music and contemplate life, because it is such a peaceful area. We walked around up there, and then we started getting sad we were about to have to leave each other again for the unforeseeable future!
STOP 3: Boston Bruins Bar – Terminal A in Boston Logan Airport
Sadly, I took a nap on the drive back to the airport, but we said our sad goodbyes before my friend and I had to say goodbye to our local friend who had picked us up. After she left, we headed into the airport, past security, and decided to continue one last stop on our New England beer tour.
We walked and walked to a quiet terminal – Terminal A – and found a nice bar sitting next to the windows. It was the Boston Bruins Bar, and we had our last couple of New England beers there. The bartenders were so friendly, and we even got into a conversation about how he always see bachelorette parties at the airport heading to Nashville.
Then, my friend and I parted ways, and I headed back to Nashville. I loved New England. We even have plans to go back to the beach in Rhode Island! The houses are quaint and colonial, the history of Boston is unbeatable, and the breweries in Connecticut are cozy and fun.
