Classic Things to See and Eat When You Visit Boston

Boston is a city that truly has it all! There’s something for everyone, from history to sports to incredible food and drink, so you’ll never be at a loss for things to do, drink, or eat. Speaking of things to do in Boston, we’re happy to be your guide as food tours are what we do best. If you want to join us for some classic sites and bites of Boston then join us for our Classic Bites of Boston Tour.  On it you’ll learn about and taste some of Boston’s most iconic dishes while learning some fascinating history too. If you choose to go at it on your own, here’s a list of some of Boston’s most classic and historic sites with places to grab a bite nearby.

A lot of these sites are stops along The Freedom Train, one of the most well-known historical sites to visit in Boston that you shouldn’t miss. It’s much more than just one site though, rather it’s a 2.5 mile red brick trail that will lead you through the streets of downtown Boston through 16 different sites that are significant to the history of the United States. With all that history you’re bound to work up an appetite, so we’re breaking this down into several stops for you.

Visit Faneuil Hall Marketplace and Eat at the Bell in Hand Tavern

Faneuil Hall Marketplace is a great place to explore and actually one of the stops on the historic Freedom Trail. It was the site of many Revolutionary-era meetings and protests before it was turned into a modern marketplace. After checking it out stop at The Bell in Hand Tavern for a classic Boston lunch. When you’re there spring for some local favorites like clam chowder and a lobster roll. And don’t forget a pint of their special beer, The Bell in Hand Ale, that is brewed just for them by Sam Adams. The Bell in Hand is located about halfway through the Freedom Train and also has some history to it, but you have to join us on our Classic Bites of Boston tour to learn that *wink*.

Visit Boston Latin School and Eat Boston Cream Pie at Omni Parker House

Next, on your list to visit is the Boston Latin School, aka the oldest public school in the country. Then head to the Omni Parker House to grab some Boston Cream Pie. Pro tip: make sure you sit while you eat this pie because it might take your breath away.

Walk Through The Boston Public Garden and Ride on The Swan Boats Then Eat At The Paramount

Photo Credit: Swan Boats

Boston Common, which is connected to the Public Garden is actually the first stop on the Freedom Trail, but just in case you can’t make it through the whole thing this is one of the must-visit places on it. Not only is the park scenic with winding paths and beautiful foliage but you’ll find the iconic swan boats floating around the pond right in the middle of the Garden. These boats have evolved over time and have been a long-standing staple in Boston. The first boat set sail on the pond in 1870 by Robert Paget and four generations later the Paget family is still operating the swan boat rides.

On your way out of the park head towards Charles Street and be sure to also visit the famous Make Way For Ducklings statues. As you continue to exit the park towards Beacon Street you can also snap a photo outside the famous Cheers Bar while heading towards Charles Street to eat at The Paramount. This neighborhood eatery has been operating since the 1930s and is still going strong. You order at the counter and then you find your seat, and don’t worry, no matter how busy it looks you’ll always find a seat, we can vouch for it!

Visit The Bunker Hill Monument & USS Constitution in Charlestown Then Eat At Brewer’s Fork

Photo Credit: Brewer’s Fork

If you’d rather see some sites at the end of the Freedom Trail then head to Charlestown and visit both the Bunker Hill Monument and see the USS Constitution, which both conclude the Freedom Trail. Both of these sites are located in close proximity to each other and in between happens to be one of our favorite pizza spots (go figure). The USS Constitution is the oldest commissioned warship still afloat and the monument on Bunker Hill pays homage to the Battle of Bunker Hill, the first major battle of the Revolutionary War. In between visiting them stop by Brewer’s Fork for a delicious brunch, lunch, or dinner. Their wood-fired pizza is amazing, their tap-list is huge, and their atmosphere is rustic and comfy. While it’s easy, don’t get too caught up in all the grub, you still have a lot of exploring to do!

Visit The Paul Revere House and Walk Around The North End Then Eat At The Daily Catch

Photo Credit: @kirsty_emily via Instagram

One more important stop on the Freedom Trail that you should definitely make time to visit is The Paul Revere House, which happens to be in the North End, aka Boston’s own “Little Italy.” After you visit and tour this historical site explore the quaint yet busy streets of the North End. Tempting smells of pizza, pasta, and pastries will pull you in every which direction you, and while there are a ton of great places to eat, one of our favorite’s is The Daily Catch, a Sicilian-style seafood and pasta place offering incredible homemade squid ink pasta and fresh catches for you to enjoy. This place is snug but that’s part of the charm so if there’s a wait it’s worth it, we promise.  When a steaming hot pan (yes they often serve pasta right in the pan) and some stuffed calamari arrives at your table the time you waited will soon be forgotten!

Visit Fenway Park Then Eat Biscuits and Honey Butter At Sweet Cheeks Q

Photo Credit: Sweet Cheeks Q

If you’re visiting Boston it goes without saying that you should take a trip over to Fenway Park. Not only is it a hub here in Boston where crowds flock for Red Sox games and other cool events, it’s also the oldest major league stadium still in use. It’s famous for it’s towering “Green Monster” in left field where you can actually stand and watch the game from. After your trip to the stadium you’ll probably be hungry, as we are after any activity, so head to Sweet Cheeks Q for some Texas barbecue and a bucket o’ biscuits. Owned by celebrity chef, Tiffani Faison, a former contestant on Top Chef, this spot attracts a lot of attention and it follows through from the atmosphere to the food, you’ll really want to stay all day and night. And after eating one of their gargantuan buttermilk biscuits with honey butter you may not be able to leave!

Visit The Massachusetts State House and Eat at 21st Amendment

Photo Credit: 21st Amendment

The Massachusetts State House is located in the Beacon Hill neighborhood of Boston, which in itself is worth a visit. Small streets, some cobblestone, are lined with picturesque brownstones, shops, and restaurants. The “new” and current State House was designed by Charles Bulfinch and has served as the seat of Massachusetts government since its opening in 1798. It holds the legislative and executive branches, and it sits adjacent to the former site of the historic Hancock mansion.

Just around the corner is 21st Amendment an iconic Boston restaurant and bar. The site of the 21st Amendment was originally designed in 1899 as Boston’s most luxurious hotel complete with electricity, running water, a roof garden and the city’s first “passenger lift.” It’s elegant furnishings and amenities attracted Boston’s most famous guests and visitors such as Louisa May Alcott, Alexander Graham Bell, and Charles Lindbergh. Originally the 21st Amendment, or as it was known then as the famous men-only Bellevue Pub, and later, the Golden Dome Pub, was a hangout for some of the state’s most colorful figures. A good part of the Commonwealth’s business was transacted in the Bellevue’s dark corners and John F. Kennedy was even rumored to write speeches by the fireplace in the back. While the name and appearance may have changed, the welcoming spirit remains.