There’s no denying the allure of the Northeast’s trove of historic sites, from Philadelphia’s Independence Hall to Boston’s Old North Church. But as much as the region celebrates and honors its history and heritage as the site of the nation’s founding, it’s also full of vibrant communities, each alive with its own unique, modern allure.
Led by locals who know and love the area, city tours offer a great way to enjoy an overview of some of the Northeast’s most iconic and appealing destinations. From history-rich cobblestone alleyways in Boston and Philly to farm-to-table food in Providence, Rhode Island, and craft beer in Portland, Maine, these unusual urban tours showcase some of the best stops the region has to offer.
Boston Freedom Trail
Considered a must-do during any trip to Boston, the iconic Freedom Trail is a 2.5-mile red-brick trail that connects 16 of the city’s most historic sites including Paul Revere’s House, the site of the Boston Massacre, Faneuil Hall and Bunker Hill, all of which played formative roles in the early days of the American Revolution.
The Freedom Trail Foundation’s experienced, costumed tour guides can lead groups of several hundred or more in customized walking tours of the Freedom Trail, offered 362 days a year. “No group is too large,” said Freedom Trail executive director Suzanne Taylor, since larger groups are typically broken into smaller subgroups of 40 or so.
Known as the Freedom Trail Players, the guides, outfitted in faithful reproductions of 18th-century clothing, not only relay the history of the historic sites along the trail, but also share personal anecdotes that reflect their historic characters’ individual roles in revolutionary Boston.
Guides assume personas such as Isaiah Thomas, a prominent anti-British newspaper publisher, or Prince Hall, abolitionist and father of black Freemasonry, who encouraged African-American support of the Colonial revolt.
“Our guides share anecdotes on what life was like in Colonial times, what they might have endured and how they were involved in the American Revolution,” said Taylor.
Custom group tours typically include the same 11 stops featured on the trail’s public, 90-minute Walk Into History tours, which run from Boston Common to Faneuil Hall. Group planners can also opt for “extended tour options, one of which lasts two hours and 15 minutes and goes from Boston Common to Old North Church, or a three-hour tour that includes all 16 sites,” Taylor said. Additionally, planners can work with Freedom Trail staff to incorporate site visits into their tour, allowing their group access inside some of the trail’s historic buildings, such as the Old South Meeting House, where the Boston Tea Party protest began.
Rhode Island Red Food Tours
Rhode Island’s capital city dubs itself “The Creative Capital” thanks in part to its high concentration of art galleries, public art murals, live performance venues and eight college campuses, including Brown University and the prestigious Rhode Island School of Design (RISD), where youthful creativity abounds.
“We’re a college town, so there’s a lot of young energy here,” said Paula Silva, owner of Rhode Island Red Food Tours, which offers customizable walking tours that highlight Providence’s burgeoning culinary scene.
“A new restaurant pops up here every few weeks,” Silva said. “In addition to Brown and RISD, we also have Johnson and Wales University culinary school, which has had a huge influence on the Providence food scene. Most of our chefs here are either graduates of that program or have trained under a chef that is.”
Silva’s roughly three-hour, 1.7-mile-long walking tours allow guests to visit and do food tastings at six or so sites chosen from their growing list of restaurant partners. “Guests learn about the specialties of the restaurants, as well as the food philosophy of the chefs there,” Silva said.
A popular stop is Oberlin, a farm-to-table restaurant. The restaurant’s head chef, Ben Sukle, is a 2018 James Beard Foundation nominee for Best Chef of the Northeast; he focuses on sustainable cuisine. “He has his own plot of land in Providence where he sources his own vegetables,” Silva said.
Another popular stop is the recently opened Yoleni’s Greek market, the first of its kind in the United States, where visitors can enjoy authentic Greek yogurt, wines, pita, baklava and more.
While walking groups through the city spotlight Providence’s food culture, guides also share insights into the community’s history and artistic side.
“We’ll point out historic architectural buildings, art murals and the history of the neighborhoods we’re passing through,” Silva said. “I think of our guides really as food and culture ambassadors.”
Maine Brew Bus
The craft brew scene is booming in Maine, with no sign of slowing down.
“When we started offering tours six years ago, there were 46 breweries in the state, and now there are roughly 140,” said Greg Klein, group sales coordinator for the Maine Brew Bus, which offers guided tours of the city’s breweries, wineries and distilleries. “In Portland alone, there are currently 22 craft breweries in operation.”
The tour company’s fleet of three lime-green minibuses can convey 14 passengers each, but Klein and his team can work with partner companies to secure charter bus transportation for larger groups, when needed. Their tours typically last three and a half hours and include stops at three different breweries, with beer tastings and behind-the-tap access to see how the beer is made.
“Our tours are more than just a tasting room experience,” Klein said. “We get to go behind the scenes at one or more of the stops to actually see the brewing process. Our clients get to talk to the owners, brewers and tasting room staff so that we’re offering a more guided experience than they’d be able to get if they were to just visit the breweries on their own.”
Tour tickets include the cost of a flight — three or four pours, typically — at each stop. A snack on board is provided as well.
During the tour, guides share insights into Maine craft brew history, from its 19th-century origins to the current brew scene’s leading innovators.
Planners can either select from the company’s preplanned tour routes or opt for customized itineraries based on the group’s interests. Additionally, thematic add-ons such as curling lessons, an escape-room visit, go-carting and axe-throwing are also available.
From IPAs and lagers to more avant-garde, trending sour beers, the breweries in Portland offer a match for practically any palate. “When it comes to craft beer in Maine, there’s something for everybody,” Klein said.
Finger Lakes Winery Tours
Finger Lakes Region, New York
New York’s Finger Lakes region is renowned for both its natural beauty and its wine; approximately 130 wineries, plus roughly 80 breweries, cideries and distilleries, operate there.
Crush Beer and Wine Tours offers guided tours of wineries surrounding four of the Finger Lakes — Canandaigua, Keuka, Seneca and Cayuga — plus the city of Rochester. Its most popular offering, its half-day Crush on Canandaigua Tour, includes stops and tastings at four wineries, from large-scale operations like Casa Larga to the smaller, family-run Inspire Moore. The full-day version of the tour also includes lunch at New York Kitchen, overlooking the lake, plus a fifth winery stop. The company’s vehicles can accommodate up to 14 passengers each, but chartered motorcoaches are available for larger groups.
“We like to offer a good mixture of new and older wineries and of sweet wines and dry wines,” said Russell Russo, owner of Crush Beer and Wine Tours. “We try to hit the whole gamut, so people can get a good feel of what the Finger Lakes has to offer.”
Another tour company, Finger Lakes Winery Tours, has its own fleet of motorcoaches and offers transportation to the Seneca, Cayuga and Keuka lakes wine trails. Seneca Lake, the largest of the region’s wine trails, is home to more than 35 wineries. But Finger Lakes Winery Tour president Mike Fitzgerald advises visitors to not overlook the west side of Keuka Lake, home to award-winning Dr. Konstantin Frank Winery.
“They are our No. 1 winery, in terms of the awards that they win,” Fitzgerald said. “They have fantastic wines there.”
Philly by Segway
Home to Independence Hall, where both the Declaration of Independence and the Constitution were signed, and the nearby Liberty Bell, Philadelphia is one of America’s great historic cities. But that doesn’t mean it can’t be toured in a thoroughly modern way.
Philly by Segway offers a fun and unusual way to experience the City of Brotherly Love, with an array of tour options that include one- or two-hour overviews of the city’s historic sectors, iconic neighborhoods and modern city center, or more thematic tours that spotlight Philadelphia’s art murals and signature food item: the Philly Cheese Steak.
Think riding a Segway might be intimidating for your group? Maybe think again.
“Age shouldn’t be a barrier,” said Barry Marrow Jr., Philly by Segway’s business manager. “I have given Segway tours to a lady celebrating her 70th birthday. My oldest Segway client so far was 87 years old. A 30-minute instruction and Segway practice session precedes all tours.
With 35 Segways in its inventory, the company can handle groups of about 30; larger parties can be broken into smaller groups that alternate Segway rotations with integrated walking itineraries. Traditional, non-Segway-based walking tours are available through the company’s partner, Philly Tour Hub.
The popular one-hour Segway tour leads guests through the Historic Old City, along the Delaware River, past the iconic Italian Market and into the historic Society Hill neighborhood, concluding near the Betsy Ross House.
“We talk about the history, but we also like to show things that are happening now, today — things that show a little bit of Philadelphia’s modern culture as well,” said Marrow.