2024 Fenway Bowl: Boston Travel Guide

I love Boston. I hate Boston.

I moved to Boston in the summer of 2008 and quickly this small town kid from central North Carolina found a city that was both a pleasure and a pain to live in. When you grow up around car culture and then you move to a city where getting behind the wheel of a car is about as inconvenient as possible, it takes some adjustment. Still, for twelve years I called that city home and keep meaning to go back some day.

Once it was announced that Carolina was going to play in the Fenway Bowl this Saturday, there’s no doubt there are fans who had never set foot in the city made plans to attend. The chance to go to one of the oldest ballparks in America in an iconic city, after all, is tough to pass up.

So, I’ve taken on myself as a former resident to give you a small guide to the area. Keep in mind this is just for those looking for the “tourist” experience. Locals can use the comments to talk about out of the way options for folks.

Let’s get started.

Transportation

Boston’s mass transit system is the MBTA. Every station is marked with a big T logo in a white circle. Know if you want to go to the Harvard area you’ll need the red line, if you want to go to the waterfront area you’ll need the blue line, anything around downtown you’ll want the orange line, and the Fenway Park and Back Bay area are on the Green. Oh, the Green also has three branches—because of course they do.

Where you stay in Boston will affect how much you want to use the MBTA. If you’re staying in the Seaport—near the airport and where the convention center is—the only T option is the Silver Line which is basically a dedicated bus line. You’d ride it into South Station to connect to the Red Line and go from there. I’d honestly recommend using a ride share to your first location though. If you’re in the city not in the Seaport, just use your phone maps to locate the closest station and you can plan your ride from there.

If you’re staying outside the city, the smart move would be to find a spot where a rapid transit line ends, park there, and hop a train into the city—or rideshare to one of them because once you actually hit city traffic, it’s a nightmare. The web site will tell you the stations with parking where you can do this.

Wherever you’re staying, I’d honestly recommend using the Green Line to go to the Fenway Bowl. Parking around Fenway Park is almost non-existent and expensive—you’ll likely pay more to park than to go to the game. There are two stations within a 10 minute walk of the station, Kenmore and Fenway, and it’s by far the more convenient way to get to the game.

Lastly, Save yourself some trouble and if you plan on using the MBTA multiple times just buy a week pass. It’s $22.50, the equivalent of 10 rides. You’d think that’s a lot until you realize that you have to pay every time you go through a turnstile. The MBTA recently added readers to allow you to use your card, phone, and watch for fares. Their explainer is here.

The Touristy Things

There’s really no reason to leave the heart of the city during your stay. A lot of the iconic things in Boston are located within a stone’s throw of each other, and once you go beyond the Fenway Park area it’s pretty much going to just be neighborhoods.

The best place to start to see all you know Boston for is The Freedom Trail. This is a trail that starts at the Boston Common, and is marked (mostly) with a red brick path that will take you by several iconic locations. You’ll see multiple colonial cemeteries, the Old Statehouse, the site of the Boston Massacre—yes it’s in the middle of an intersection—Quincy Market, the North End with the Paul Revere House and the Old North Church, the USS Constitution and the Bunker Hill Memorial in Charlestown. It’s just about every historic colonial sight you’d want to see.

You can visit the site of the Boston Tea Party a little off the Freedom Trail, complete with tours and reenactments. With it being the holidays, check the site to make sure you can get the experience.

The New England Aquarium is a must-visit for anyone who might vaguely be interested. They are located on the Waterfront with their own stop on the Blue line, and the setup is unique—they have one huge tank in the middle of the building with all sorts of sea life including Myrtle the Turtle, and the various exhibits are around that tank as you ascend to the top. Penguins are at the bottom, and there’s a touch tank right as you enter. There’s also an IMAX theater to the side.

In the Back Bay there are several places worth taking a peek at—the fine shops along Newbury Street, the Boston Marathon Memorial, and so forth—but The Prudential Center offers the ability to both shop and get a sky view of the city. It’s easily accessible from the T and the entire complex is one where you can stay inside for a while to escape the cold.

As far as other sports go, the Patriots play 45 minutes south of the city and sadly the NFL decided to schedule their game to happen at the same time as the Fenway Bowl. The Bruins are on the road, but the Boston Celtics have a home game against the Pacers on Friday Night if you’re looking to see the TD Garden area and some NBA Action.

Food

You want that bowl of clam chowder cause you’re in Boston? There are two places you have to go, either would be a great choice.

Union Oyster House is on the Freedom Trail, and is one of the oldest continuously operating restaurants in the country.. It’s a good combination of history and the food is really good. They even have the booth marked where JFK ate his meals. Meanwhile, Legal Sea Foods is a local chain that has the distinction of having their chowder served at multiple presidential inaugurations. It also has some of the best baked stuffed lobster you could ask for. My favorite location is on the waterfront near the aquarium.

The North End is the city’s Italian district and is just loaded with all sorts of amazing restaurants too numerous to mention. Boston Magazine has a list here, and honestly the more neighborhood type of place you can find is probably best. They’ll have the “if it’s not on the menu, ask us” type attitude. The iconic food place there, though, is Regina Pizzeria, You’ll usually see a line but it’s an icon for a reason. Also, there are two pastry shops across the street from each other—Mike’s Pastry and Modern Pastry. For the best cannoli selection head to Mike’s, and for the best “other” Italian pastry selection go to Modern.

Finally, if you’re looking for steak, I can’t recommend Abe & Louie’s highly enough. It’s what you picture a high end steakhouse would look and feel like with the wait stuff in full dress, dark wood surrounding everywhere and steaks that melt in your mouth. Others will swear by Grill 23—which is not related to Michael Jordan in any way—and it’s tough to argue with them. Either one is great if you’re budgeting for an extravagant meal.

I could go on but I’ll stop there to take it easy on my editors as they have to look over this on a holiday. Should you have specific questions, hit me up on Twitter/X. It’s been a few years so things in the city have changed somewhat but those staples are still there. Also, if any locals want to throw suggestions, put them in the comments! Some folks want to travel and specifically want to do the non-touristy things.

Either way, if you’re going, bundle up and enjoy the city I called home for over a decade! Go Heels!