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The Inn-side Track on Fall Weekends in Boston

Hundreds of websites claim to have the inside track on fall weekends in Boston. But only a local can tell you about limited-time pop-up shops, the treats to splurge on, and where you can have a one-of-a-kind experience that you’ll be talking about at home. Here’s our version of a Boston weekend, available only to our favorite visitors — the ones that book with The Coolidge Corner Guest House!

Stroll the Emerald Necklace
Famed landscape architect Frederick Law Olmstead, who designed New York’s Central Park and Montreal’s Parc Mont-Royal, saved the best for his hometown. Boston’s famed Emerald Necklace is a collection of linked parks that will take you through a fascinating swath of the city’s neighborhoods. For an urbane stroll, start at the Public Garden, head down Commonwealth Mall, and end with some sights and a snack in Kenmore Square. To see the wilderness within the city, begin at the Back Bay Fens and walk to Jamaica Pond, where you’ll be just blocks away from the shops, restaurants, and bars of Centre Street.

You can skip the Italian superstore owned by a celebrity chef, and instead take the T from Coolidge Corner to Haymarket. Cross the Greenway to Hanover Street and you’ll find yourself in Boston’s Italian neighborhood, the North End. Boston’s famed red-brick Freedom Trail passes right through; along the way you’ll find to Paul Revere’s house and some of the best cappucini, elephant ears, and cannoli around. Mike’s Pastry, Modern Pastry, and Caffé Vittoria vie for dominance. You should probably try all three to make a fair comparison.

(By the way, if you spot a long line at Pomodoro or the Daily Catch, don’t despair — they both have outposts in Brookline that are just as good, and much easier to get into!)

Skip the Sox
We’re pretty proud of our World Series champions this year, but even if you’re not a fan of the #DamageDone crowd, Fenway Park is worth a visit in the off-season. This fall, the stadium will host a series of epic sporting events, including the Harvard-Yale football game, an Irish hurling tournament, and a series of local high-school matchups. Enjoy Major League Baseball’s oldest ballpark in fall — you don’t even have to root for the home team!

Water Views
Boston’s Seaport is growing every day, and a visit here will ensure you’re on the cutting edge of the city’s shopping and dining trends (at least for a week or so!). Check out the latest from the modern art world at the Institute of Contemporary Art, [] and then fortify at Gather, the restaurant inside of “the world’s first free-standing innovation center,” District Hall. Visitors in November and December can get some early shopping done at the BBOB Pop-Up, a celebration of Boston’s Black-owned businesses held at District Hall one Saturday each month.

Parting Shot
If you’re flying out of Logan Airport, give yourself extra time to take a lovely last look at the city via Piers Park, a highlight of the East Boston waterfront. Then, head to Santarpio’s, a famous East Boston pizzeria. It’s not haute cuisine, but it’s delicious, and strictly for locals. (Need proof? The drink options are beer, red, and white — and that literally means three choices, not a range of brews or varietals.) Act like a Bostonian and stuff yourself before you board your plane. The airport’s five minutes away.



Throughout its history, Brookline has resisted being annexed by Boston, in particular during the Boston–Brookline annexation debate of 1873. The neighboring towns of West Roxbury and Hyde Park connected Brookline to the rest of Norfolk County until they were annexed by Boston in 1874 and 1912, respectively, putting them in Suffolk County. Brookline is now separated from the remainder of Norfolk County.

Brookline has long been regarded as a pleasant and verdant environment. In 1841 edition of the Theory and Practice of Landscape Gardening, Andrew Jackson Downing described the area this way:

“ The whole of this neighborhood of Brookline is a kind of landscape garden, and there is nothing in America of the sort, so inexpressibly charming as the lanes which lead from one cottage, or villa, to another. No animals are allowed to run at large, and the open gates, with tempting vistas and glimpses under the pendent boughs, give it quite an Arcadian air of rural freedom and enjoyment. These lanes are clothed with a profusion of trees and wild shrubbery, often almost to the carriage tracks, and curve and wind about, in a manner quite bewildering to the stranger who attempts to thread them alone; and there are more hints here for the lover of the picturesque in lanes than we ever saw assembled together in so small a compass.”

Coolidge Corner, which is located at the crossing of Beacon Street and Harvard Street, is one of Brookline's two primary retail districts (the other being Brookline Village). It includes a number of historically significant sites, including the S.S. Pierce Building, and the Coolidge Corner Theatre.

the Country Club, an exclusive sporting club in the town, was the first private club in the United States formed exclusively for outdoor activities. It is most famous as a golf club; it was one of the five clubs that formed what is now the United States Golf Association and has hosted the U.S. Open three times and the Ryder Cup Matches once.

Larz Anderson Park is in Brookline on the 64-acre (26 ha) estate once owned by Larz Anderson and Isabel Weld Perkins. The park contains the Larz Anderson Auto Museum, the oldest automobile collection in the country, as well as Putterham School, a one-room schoolhouse from colonial times.

The birthplace of John F. Kennedy stands in Brookline and is listed in the National Register of Historic Places. It is maintained by the National Park Service and is open to the public from May through September.

St. Aidan's Church was where John F. Kennedy was baptized and where the Kennedy family and other prominent Irish-Americans were parishioners. The church was designed by architect Charles Maginnis, who was awarded the American Institute of Architects' gold medal. Though it is on the National Register of Historic Places, St. Aidan's Church has been closed and converted into housing.

The Puppet Showplace Theatre, one of the four oldest puppet theatres in the United States, is located in Brookline Village.

The Dutch House, one of only five surviving buildings from the World's Columbian Exposition of 1893 was relocated to Brookline.

John Goddard House, an historic house at 235 Goddard Avenue, was built in 1767 and added to the National Register of Historic Places in 1985.