One of the best ways to discover Boston — its secrets, its history, and its charms — is on a guided walking tour with a knowledgeable, passionate-about-Boston local. Tours of the Freedom Trail top the list (done it, done it, done it). But there is a slew of other fun and interesting guided tours of the city. Here are some of our favorites.
Underground Donut Tour
“There’s never a bad time for a doughnut. Early morning? Sure. Afternoon, why not? Late night? Perfect!” says Jeff Woelker, owner of Underground Donut Tour. “Everyone is always in a good mood when they’re eating a doughnut.”
Woelker started the Boston doughnut tour in 2021, and it’s been a big hit. You’ll join a small group of up to 20 fellow pastry lovers (private tours are also available) on a two-hour jaunt to four of Boston’s top doughnut makers. Tastings are generous, between five and seven different flavors on each tour. “Many guests hit a wall toward the end of the tour,” Woelker says, “so we provide to-go bags and boxes so you can take home anything you can’t finish.” Tours are offered year-round, Friday, Saturday, and Sunday. 844-366-8848, www.undergrounddonuttour.com; ages 11 and older $40, 10 and under $25.
Rum, Riots, Writers & Revolution Tour
You’ll hear fun and astonishing stories on this one mile or so romp through downtown, peppered with secret lore, including the location of JFK’s love nest, the crimes of Charles Ponzi, and the escapades of Mayor James Michael Curley, who served the first five months of his term from a jail cell.
Another favorite story on the tour is about the statue of General Joe Hooker, located in front of the public entrance to the Statehouse. But we won’t spoil the suspense. Join the tour, offered by Free Tours by Foot. Pay what you want at the end of the tour. Tours are offered March-September, Wednesday through Monday, October through February, weekends only. www.freetoursbyfoot.com
Beacon Hill Crime Tour
Beacon Hill may be posh and beautiful, but it doesn’t have such a pretty history. This was killing grounds for the Boston Strangler; two of his victims were found here. It was also home to rich, old Dr. George Parkman, who was strangled, stabbed, cut up, burnt, and dissolved in acid, for an unpaid debt. And Piero Brentani, who was killed by his angry girlfriend in a Beacon Hill apartment. You’ll hear more stories of sordid crime and punishment on this two-hour walk through one of Boston’s most exclusive neighborhoods.
Warning: this tour is R-rated and not recommended for kids under the age of 16 — or anyone who is not comfortable with graphic information. The tour is offered by Free Tours by Foot; you decide at the end of the tour what, if anything, you’d like to pay. Tours are offered May through October, Monday, Friday, and Saturday. www.freetoursbyfoot.com
Ghoulies, ghosties, long-leggedy beasties … and things that go bump in the night. This fun-loving tour dredges up stories of misery and death in Beantown, and the city’s lingering not always happy spirits. Oh my. You’re bound to feel a few shivers down your spine, and be looking over your shoulder, as you explore Boston’s sordid history of miscreants, killers, and thieves.
You’ll visit six to 12 haunted locations, covering about a mile and lasting about one hour. If you’re really into gruesome crime and mayhem, you can bundle this tour with tours of Salem and The Historic Lizzie Borden House. They also offer a Haunted Pub Crawl. www.ghosttours.com, nightly, $20.99
North End Pizza Tour
Thin crust, thick crust, triangles and squares, any way you slice it, this tour is 2½ hours of deliciousness. You’ll head to Little Italy and the North End, home to Boston’s most celebrated, award-winning pizza. The tour includes stops at three different pizzerias, each offering a unique style and ambiance. The pizzerias are nicely spaced out (you’ll be ready for another slice!), and guides also stop at five Freedom Trail sites, including Paul Revere House, Old North Church, Bunker Hill Monument, and the USS Constitution. You’ll get a heaping serving of history and fun facts to go with your pies. 855-487-4992, www.bostonpizzatours.com, daily, $49
Fenway Park Tour
Do you know the story behind the lone red seat at Fenway Park? We didn’t until we took this fun-for-all, behind-the-scenes tour of “America’s Most Beloved Ballpark.” It marks the longest home run ever hit at Fenway. It measured 502 feet and was hit by Ted Williams on June 9, 1946. Even if you’re not a lover of history or trivia (or a baseball fan), you’ll enjoy this 1-hour guided visit that includes a look inside the press box, a stop atop the legendary Green Monster, and lots of stories and facts about Red Sox greats. www.mlb.com/redsox/ballpark/tours, daily, adults $25, ages 12 and under $17
Diane Bair and Pamela Wright can be reached at firstname.lastname@example.org