The Freedom Trail is a 2.5 mile red brick-path that takes you through sixteen important and historically significant sites in downtown Boston. After years of eating gluten-free while living in the Boston area and being an avid history buff, I’ve created my own gluten-free version of the Freedom Trail. This self-guided walking tour combines many of the historical sites you’d find on the Freedom Trail, plus a few local stops every Bostonian knows and loves. It’s a little bit longer than the traditional Freedom Trail and you can choose to do all of it, parts of it, or whatever you prefer. Along the way, you’ll be able to sample some of the best gluten-free foods in Boston. Brush up on your middle school history lessons and come hungry – Boston has a lot to both teach and feed you!
Boston Public Market
Start your morning at Boston Public Market, located near the Haymarket green and orange line subway ‘T’ stop.This central location allows you to see a lot of Boston proper before heading out to the specific Freedom Trail. The indoor small cafeteria of Boston Public Market has vendors of all kinds selling baked goods, fresh honey, groceries, natural products, cheeses, and more. Jennifer Lee’s Gourmet Bakery is a 100 percent gluten-free facility that always has muffins and pastries on hand for a mid morning snack. Mother Juice, a vegan and gluten-free juice bar, utilizes products from local farms in the area. If you prefer a more substantial breakfast, check out Inna’s Kitchen, a Jewish deli offering delicious gluten-free baked goods & sandwiches.
Faneuil Hall & Quincy Market
Upon exiting the Public Market, continue down Union Street to Faneuil Hall, where the Sons of Liberty met to discuss their plans during the American Revolution. Entrance is free and often a National Parks Ranger will give regular talks about the history of Faneuil Hall and how it is still used today! Downstairs you can find various historical gifts, goods, and Boston related souvenirs.
Directly behind Faneuil Hall is Quincy Market, an indoor food court. Here you have a chance to try the famous New England clam chowder (made gluten-free) at Fisherman’s Net. They use cornstarch instead of flour so it’s safe to eat! For a sit down meal, try Bostonia Public House, offering an extensive gluten-free menu with seafood, burgers, and more.
The North End
Across Surface Road and Cross Street will lead you to the North End. This area is small but packs a lot of history and delicious Italian cuisine. The North End is known as the Little Italy of Boston. It has two main streets you’ll want to walk down: Hanover Street and Salem Street. Both have various restaurants and small cafes, plus gelato shops, bakeries and pizzerias. The smells wafting from the windows will make your mouth water and the random bursts of Italian you hear from the gentlemen on the corner will make you smile. Modern Pastry is one of two famous bakeries in this area that make gluten-free cannolis and whoopie pies. Mike’s Pastry across the street also offers gluten-free whoopie pies and cookies. You will often find festivals throughout the North End at different times during the year honoring various saints and religious figures.
For an authentic Italian grocery store, stop in Salumeria Italian on Richmond Street. They sell fresh meats, cheeses, and imported Italian products like gluten-free pastas. Around the corner is the home of Paul Revere. For a small price, you can tour the inside and learn more about his famous ride.
Al Dente and Benevento’s on Salem Street will make all of your dreams of classic Italian dishes come true as gluten-free masterpieces. The pasta bolognese, antipasto salad, and thin crust margherita pizzas are out of this world good! Their attention to detail, knowledge of gluten-free diners, and excellent recipes make either of these places a great stop for lunch.
Once you’ve had your fill of Italian food, take a look at the ground you are walking on. If you see a thin red-brick line in middle of the sidewalk, you’ve found the official Freedom Trail. Anywhere along this path will take you past a site of historical significance. Boston is a city on a smaller scale where you can see so much in one day! If it becomes too much walking, the T (subway) is easily accessible and straightforward to use.
Before you leave the North End, stop in the Old North Church. This famous steeple is where two lanterns were hung to let the colonists know the British would be arriving by sea, and not by land.
Continue over to Charlestown to see the Boston Navy Yard or the monument on Bunker Hill which commemorates the battle of the American Revolution. If you want to get your sea legs, head to the USS Constitution, which is the oldest working naval vessel still afloat. Admission is free and you’ll have a chance to go below deck and meet current sailors stationed there. If you are feeling hungry on your way back from Charlestown, Tavern in the Square is the perfect stop for a drink or a snack. Their Parmesan truffle tater tots are delicious and almost everything on the menu is gluten free.
Back down Congress Street through Government Center, you will pass the Old State House, site of the Boston Massacre, Granary Burial Ground, where patriots like Samuel Adams are buried, and both the Boston Common and Boston Public Garden. The Public Garden is especially beautiful in the spring and summer due to the flowers in bloom and warmer temperatures. Bostonians appreciate any warm weather they can get!
The houses lining the Boston Common are some of the most beautiful homes in the city. These brownstones are along the same side of the Common as a famous bar where everybody knows your name! The Cheers Bar is a great stop for a gluten-free local cider and you can take home the glass.
For a sit down meal filled with delicious local fish, try Legal Seafood in the theater district, right alongside the Public Garden. There are so many seafood options available with their gluten-free menu you won’t feel deprived. Get the fish and chips – fried in a dedicated fryer, they are crispy and perfect. If you prefer a steakhouse, try Davio’s. They have gluten-free menus for brunch, lunch, and dinner. Plus, their pasta dishes are served with gluten-free pasta or gluten-free gnocchi!
If you’re still up for more, continue into Copley Square and check out the Boston Public Library. The finish line of the Boston marathon is in this area as well, and on weekends you can find flea markets and farmer’s markets during the spring and summer. Luke’s Lobster, while a little pricey, offers the famous New England classic of a lobster roll, made gluten-free.
Papa Razzi on Newbury Street is a nice sit down restaurant with more delicious Italian food and an excellent gluten-free menu. Everything is made to order and it’s all fantastic. It’s become my go-to place for birthdays and all types of celebrations, especially for the fried mozzarella appetizer made gluten-free and served with homemade marinara sauce.
Back Bay & Fenway
If you are a baseball fan, continue down to the neighborhood of Back Bay and check out Fenway Park, one of the oldest ballparks in America. Don’t wear any Yankees gear or you will undoubtedly be a target for some name calling. Boston fans take their baseball very seriously! If you are able to see a game, I would highly recommend it. Even if you aren’t a Red Sox fan, the atmosphere and the sheer intensity of Boston fans is an experience to remember!
Fenway Park has an entirely gluten-free kiosk offering hot dogs on Udi’s buns and gluten-free brownies. It’s located behind Grandstand 21 and I stop by during every Red Sox game for my own gluten-free treats. After a full day of sightseeing, there’s nothing like watching a baseball game with your own gluten-free hot dog.
Another area of Boston I enjoy exploring is Cambridge. This neighborhood across the Charles River is home to the prestigious universities of Harvard and The Massachusetts Institute of Technology. Walking around the red brick buildings surrounded by college students just makes you feel smarter!
More delicious gluten-free stops in Cambridge include Violette Bakery, a 100 percent gluten-free bakery, and The Friendly Toast, an awesome local diner that has plenty of gluten-free options and a tasty brunch. Also, check out Naco Taco for eclectic tacos fried in a dedicated fryer.
Whether you decide to see as much of Boston as you can, or just one neighborhood, you’ll be able to find plenty of local gluten-free eats. This Gluten-Free Freedom Trail will show you the best of Boston’s history, character, and charm, and all the delicious gluten-free stops to go with it. At the end of your tour, you’ll be wicked smart not only in Boston facts and trivia, but how to navigate a major city with a limited diet.
Jennifer Fitzpatrick was diagnosed with celiac disease in 2009. She is currently traveling the world for the next six months with her husband. Check out her website www.thenomadicfitzpatricks.com or her Instagram @jefinner589 for more tips on traveling gluten-free. Fitzpatrick’s series on Gluten-Free New England will be shared at Gluten-Free Living for the next six months.