Boston’s Freedom Trail: Tips, tricks and hidden secrets

An old city in the new world, Boston is a place chock full of historical landmarks and layered with centuries of well-kept secrets and hidden gems. From 17th century graves to a 20th century covert steakhouse, mystery is around every corner, waiting to be discovered by tourists and locals alike.

The good news is, Boston’s biggest historical attractions like Bunker Hill, Paul Revere’s House and Quincy Market are strung together along a red brick and painted path dubbed the Freedom Trail. Many tour companies are available with knowledgeable guides ready to walk visitors from site to site, explaining the who’s and what’s behind the Patriots’ road to revolution.

Whether following a guide or traveling the Trail alone, here are a few tips and tricks to add to your adventure.

Rest your feet on the Charlestown Ferry

While the Freedom Trail is completely walkable, it can make for a long day. To cut down on steps AND get a great view of the city, catch the Charlestown Ferry at Long Wharf after you hit all of the stops from Boston Common to Old North Church in the North End. The ferry leaves every 15 minutes and costs less than $2 to ride each way. Passengers can sit inside or out, but either way, they get a stunning view of the Boston skyline from the water! The ferry stops off at the Charlestown Navy Yard and from there it’s a short walk to Bunker Hill and the rest of the stops on this side of the bay.

View of Boston from a Ferry

Search for Mother Goose

Lay a penny on Paul Revere’s headstone, pay respect to John Hancock and look up at the towering Franklin Monument at the Old Granary Burying Ground, but don’t forget to visit Mother Goose. Walk up the center trail of the burying ground to the short dead end path located between the Franklin Monument and the back of the cemetery. Here lies the first wife of Isaac Goose, Mary, and his second wife, Elizabeth in an unmarked grave nearby. Mary gave birth to 10 children before passing away. Elizabeth raised all 10 kids and added 10 of her own to the clan. Elizabeth may have never penned a nursery rhyme, but she’s certainly earned the title “Mother Goose.“

Find your Saint in an alleyway

Stop by to see if Peter Baldassari has the wooden gate to All Saints Way alley open at Hanover and Battery Street in Boston’s oldest neighborhood, the North End. Baldassari is sometimes on hand to talk all about his passion project, collecting saints and building out his sanctuary to them. He will even help visitors find their Saint based on their birthday. It’s a beautiful place that mashes up art, history and religion in a homemade alleyway museum. If the gate is closed, take a peek through the slats to check out Baldassari’s collection. 

See where Benjamin Franklin was born

This unassuming landmark is just steps off the Freedom Trail between the Old Corner Bookstore and the Old South Meeting House, but many people miss it! The birthplace of Founding Father Benjamin Franklin at 1 Milk Street is marked by a small white bust of Franklin himself. The original building where Franklin was born burned down in 1810.

Dine in a secret steakhouse

Just 2.5 blocks from the Park Street Church stop on the Freedom Trail is a hidden 20-seat steakhouse where patrons can order hand crafted cocktails, caviar, foie gras and a 28-ounce bone-in Porterhouse. Walk through the casual JM Curley burger joint and look for the “Adults Only” sign. Turn off your cell phone and enter Bogie’s Place, a private dining experience of a lifetime. Main course prices range from $23 to $75 with add-on sides for $7 to $14. Make sure to call ahead and make reservations.

Take note of the 10-foot wide house

Directly across the Hull Street entrance to Copp’s Hill Burying Ground in the North End stands 4-story house touted as the narrowest house in Boston, measuring only 10 feet wide. Urban legend holds the house was built by a bitter brother to block the sunlight to his sibling’s larger home on land the two inherited from their father. The Civil War era house is still occupied today.

Step carefully over the dead

Four cemeteries are located on Boston’s Freedom Trail, including the city’s three oldest. Visitors may notice that the faded headstones that in some cases date back to the 1660’s, are all organized in fairly neat rows. That was not always the case. In fact, it’s likely that not many of the headstones still mark the resting place of those who were buried there, and the remains of bodies probably extend underneath surrounding streets and structures.

Boston Cemetary

Grab a bite at Paul Revere’s old haunt

Hob nob where Paul Revere used to hang out, at the Green Dragon Tavern not far off the Freedom Trail at 11 Marshall Street, just behind Union Oyster House. The history of the pub is disputed, but it’s said that Paul Revere launched his famous midnight ride from here to warn the patriots of the British march toward Lexington and Concord. The current standing restaurant is proud of its history that extends at least back to the 1770’s, if not back to 1654 like the pub claims. Regardless, it’s a great place to take a load off and grab a bite to eat at a historic landmark!