City runs, complete with history and views

Brian McCarthy lead a City Running Tours group downtown.
Brian McCarthy lead a City Running Tours group downtown.

Weaving past Boylston Street shoppers, my tour guide Wayne Levy dispenses historical trivia. “Did you know that the Boston Public Library opened in the mid-1800s as the first free, public city library in the US?” he says. “Did you know that Trinity Church is considered one of the 10 most significant buildings in the US by the American Institute of Architects?” No, I didn’t. We turn left toward the Public Garden and Levy mentions how Back Bay’s cross streets from Arlington to Hereford feature the names of British earldoms. I didn’t know that either.

Then, as we move toward the gold-domed Massachusetts State House, Levy poses questions you don’t typically hear on city tours. “How’s the pace?” he says. “How about a 4-mile route that follows part of the Freedom Trail, then crosses the Charles River for a view of the Boston skyline?” The nine-minutes-per-mile pace is slow, but perfect for easy conversation and sightseeing. The planned course provides a good mix of historical sites and scenery. And that was exactly what I wanted on my first running tour of Boston.

“A lot of visitors have an interest in learning about Boston,” said Levy, who owns RunBoston Tours and a 2:34 marathon personal best. “And with all the American history and running history, I think there’s no better place to do a running tour than Boston.”

City Running Tours
Runners imagined having finished the Boston Marathon on a City Running Tours outing.

With the Charles River, HarborWalk, Boston Marathon course, and famous sites clustered along the 2.5-mile Freedom Trail, the city offers runners plenty of options. And routes that stretch three to six miles can encompass a surprising amount of historical ground. My tour covered nearly four centuries and a dozen popular tourist sites from Copley Square to King’s Chapel Burying Ground to the Massachusetts Institute of Technology. Over 45 minutes that included a handful of short stops, I saw Boston from a new perspective, enjoying a welcome change of running scenery along the way. For a regular runner who struggles with sitting through bus and trolley tours, it was the ideal combination of workout, history lesson, and casual conversation.

Get The Weekender in your inbox:
The Globe's top picks for what to see and do each weekend, in Boston and beyond.
Thank you for signing up! Sign up for more newsletters here

Running tours let active travelers and Boston-area residents experience the city in a more intimate way. And visitors who have taken running tours say guides eliminate worries about safety and confusing streets and help them explore popular attractions and find off-the beaten-path places.

Freedom Trail Run via Facebook
Runners made their way to the Bunker Hill Monument on the Freedom Trail Run.

“I’m preparing for a marathon and the Boston Marathon is an iconic route that you want to do,” said Garbi Schmidt, a university professor from Copenhagen who ran the last nine miles of the famed course with Levy. “But if you don’t know the city, you might get lost. Wayne has run the marathon several times, so he knew the course and could tell me about the Boston Marathon experience. That’s the fun part.”

For me, the fun part was learning something new about places I typically hurry past without a second thought. It helped that Levy switched easily between fun facts and important history, all in tidbits easily dispensed and digested while on the move.

After stopping briefly at the State House, Levy and I head toward Park Street Station and pick up the Freedom Trail. As we run past the Omni Parker House, the original Boston Latin School site, and Benjamin Franklin statue, Levy continues his tour guide patter. He mentions that Malcolm X was a busboy at the Omni Parker House and that John F. Kennedy proposed to Jacqueline Kennedy at table 40 in the hotel’s restaurant. Levy points out the Beantown Pub across from the Granary Burying Ground and jokes that it’s the only pub in America where you can drink a Sam Adams and look at Sam Adams’s grave. A nearby group of guidebook-toting tourists lift their heads and laugh, then stare curiously at Levy and me as we run toward Cambridge Street and the Longfellow Bridge.

RunBoston Tours
Runners went sightseeing on a RunBoston tour along the Charles River.

Given its place in US and running history, it should come as no surprise that three popular running tour companies call Boston home. In addition to RunBoston, visitors can go with City Running Tours and Freedom Trail Run, each with its own approach and personality.

RunBoston ( gives customized tours for individuals and couples with hotel pickup. Customers choose when and where they want to go and how fast they want to run. Then, Levy pairs them with one of 12 guides. He always tries to accommodate personal interests such as the one woman with a fascination for burying grounds who wanted to linger at gravesites and another woman training for a marathon who wanted to keep up a particular pace throughout the tour. Prices for personalized tours range from $50 to $70 depending on the distance, with discounts offered for additional runners. The last nine miles of the Boston Marathon is one of RunBoston’s most popular tours, a close third behind runs along the Freedom Trail and Charles River.

Freedom Trail Run ( takes large groups on a 5K course that covers, yes, the Freedom Trail. The $40 tours start at the corner of Park and Tremont streets and finish at the Charlestown Navy Yard with a ferry ride to Long Wharf. Private group tours are available for $20 to $40 per person.

City Running Tours ( draws crowds with its 10K Boston Seaport Beer Run that starts at Fish Pier and finishes with a tour of the Harpoon Brewery. The company, which has outposts in large cities across the country from Philadelphia to Minneapolis-St. Paul to Seattle, also offers a 10K run through the North End and 5K runs through Beacon Hill-Back Bay and Cambridge-MIT. Prices range from $25 for 5K runs to $45 for 10K Beer Runs. Additionally, you can arrange personalized runs that cost $75 for up to 6 miles, with $5 each additional mile.

“I love sharing the city with people,” said Brian McCarthy, manager for City Running Tours in Boston and a marathoner. “Half of my clients are local and they have never seen the city this way. They didn’t know where Paul Revere was buried or about the Custom House. I’m a history buff and I’ve turned a lot of my guides into history buffs, too. Plus, a lot of them have their own things to offer, especially the ones that live in the city.”


McCarthy admits he sometimes turns people away from his 10K Boston Seaport Beer Runs because he prefers manageable groups of roughly a dozen runners accompanied by a couple of guides. Multiple guides ensure that every runner has a good experience, even if they keep a slower pace. Most guides find that running tours naturally settle into a nine- to 10-minute-per-mile pace. That said, the Freedom Trail Run tour promotes its 16 stops and suitability for beginners, covering 5K in roughly 90 minutes.

The 10K Boston Seaport Beer Run traverses an impressive amount of territory, about 6.8 miles, in 90 minutes. The tour gives runners a look at old and new Boston, heading down Seaport Boulevard to the Rose Kennedy Greenway to Post Office Square to the Boston Common to the Freedom Trail. The route winds its way to the TD Garden for pictures with the Bobby Orr statue and to the North End, coming to a scenic crescendo as runners jump on and off the HarborWalk on the way back to the Seaport District.

“For me, it was absolutely the way to do my first 10K,” said Amy Blackwell of Hudson, N.H. “I knew that it would be a run with a twist and that I could finish it. You don’t even realize you’re running as far as you’re going because you’re listening to everything Brian is telling you. You get kind of lost in that. I felt we were learning more of the hidden secrets of the city rather than the touristy stuff. Then, to cap it off, doing a tour of the Harpoon Brewery was a blast.”

Running tours tend to be particularly popular with women, who face more safety concerns when running in an unfamiliar city. That initially drew Erin Lynch of Halifax, Nova Scotia, to RunBoston.

“I didn’t know the city of Boston at all and wanted to run, but I didn’t want to go alone,” said Lynch, now a repeat customer. “I Googled running Boston. I was flabbergasted that something like running tours existed and got really excited about it. The tours have become highlights of my trips to Boston.”

The final leg of my tour stretches over the Longfellow Bridge into Cambridge, then returns to the Back Bay via the Harvard Bridge. It’s a section along the Charles River that I run almost every day. But as part of a running tour, it somehow looks different as I learn about the full length of the river and the various nicknames for bridges. With warm weather coming, I expect other familiar routes will look different, at least when they are colored by groups of fleet-footed tourists.

Shira Springer can be reached at