The September/October shoulder season in Boston is the perfect time for a romantic, long weekend getaway in one of the East Coast’s most vibrant cities.
After summer crowds dissipate and families head home, spend a few days uncovering the best time to visit Boston – from its historic sites to colorful neighborhoods, and the scenic harbor clear across town, to game day excitement at venerable Fenway Park. You’ll embrace not only each other, but a city with something to offer everyone. A few days of fall in Boston won’t be nearly enough time, but you’ll cover enough ground to get a feel for why this is such a fascinating place and why you’ll want to return.
What to Do
There is no better way to orient yourselves to a new locale than with a tour, and this coastal city offers plenty of them. Boston by Foot has many different options; the Freedom Trail walking tour is a great way to brush up on important events in our country’s past while seeing part of downtown. Depart from outside Faneuil Hall and the Quincy Market (where you can grab lunch or a snack and do a little shopping) and learn about the city’s Revolutionary history. You can also learn about the city from the water on a Boston Harbor City Cruise, which departs from near the New England Aquarium. The hour-long sailing gives passengers beautiful views of the harbor and of the USS Constitution, the Bunker Hill Monument, and the harbor islands.
On your own, stroll along the Rose Kennedy Greenway, one-and-half miles of green landscape punctuated by public art, shaded spaces to cool off, beer gardens and food trucks, and a beautiful carousel. Walk through the Boston Public Market, close to the Greenway’s north end, for a wide selection of New England local artwork, crafts and fresh food, such as delicious ice cream from Crescent Ridge (the kiddie size is more than ample).
Faneuil Hall Marketplace and Quincy Market are another great place to stroll. Shop for souvenirs from more than 40 pushcarts and stores and then head into the market for a quick bite from the oldest and largest food hall in the country, dating back to 1826.
Grab an Uber over to the USS Constitution and Museum, where you can step onboard “America’s Ship of State” that first set sail in 1798 from Boston Harbor and featured prominently in the War of 1812. The museum is geared primarily towards younger clientele, with many interactive exhibits, but it’s worth a short visit, and you’ll find an extensive gift shop. Similarly, the Boston Tea Party Ships and Museum attracts many families, but offers fascinating information about a pivotal event in U.S. history. Adults will particularly enjoy stepping aboard full-scale replicas of the 18th century sailing vessels the Eleanor and the Beaver, and grabbing tea and a bite in Abigail’s Tea Room or perusing the gift shop for a terrific assortment of souvenirs.
If time permits, don’t miss the expansive galleries of the Museum of Fine Arts, the hallowed halls of the Boston Public Library – established in 1848 and the first free lending library in the country, or the Paul Revere House, Boston’s oldest building, constructed in 1680. The Isabella Stewart Gardner Museum is a wonderful place to spend an afternoon, enjoying an amazing collection of artwork ranging from paintings and sculptures to ceramics and rare books.
If you plan your Boston fall travel in September, you may be able to catch a Red Sox home game at Fenway Park, the oldest major league stadium still in use, first opened in 1912. Just about any of the seats will give you a good view of the action, including the original grandstand seats, more than 100 years old.
On one evening, walk through Boston’s North End neighborhood to any number of Italian restaurants, coffee and gelato shops. Regina Pizzeria, open since 1926, is casual, and the crowded, close together tables and booths translate to loud conversation and hustling wait staff. Embrace it all as you dig in to an array of mouth-watering pizzas, so good, you’ll wish you had room for just one more slice. Finish up your evening with a stroll to cash-only Caffe Vittoria, first opened in 1929, for a wide selection of coffee, tea and cordials, pastries and gelato.
On other evenings, consider dining at Union Oyster House – America’s oldest restaurant and a National Historic Landmark. Walk around before or after your meal to see the original oyster bar and head upstairs to see President Kennedy’s favorite booth. In Boston’s Seaport Neighborhood, visit Hook + Line for a lunch or dinner of a modern take on New England seafood dishes and craft cocktails served in a bright, colorful space. It’s located just across from the Institute of Contemporary Art not far from Fan Pier Park and the waterfront. If you happen to be dining during one of the ICA Free Thursday nights, stop in between 5:00 and 9:00 before or after dinner to catch the latest contemporary art exhibits on display.
Where to Stay
Boston is full of great hotels, many conveniently located near area attractions. If a harbor-side view is a must, check in to the Boston Harbor Hotel, situated on the water at Rowes Wharf. If weather permits during your time in Boston in September or October, dine outside at Rowe’s Wharf Sea Grille on the Harbor Walk Terrace, a popular spot for both locals and tourists. For a very unique experience, head to the concierge desk and reserve a private, hour-long tour of the hotel’s map gallery ($200 fee) or cozy up in The Dark Bar for food and libations including creative cocktails and liquors – such as the ultra exclusive Louis XIII De Remy Martin, which sells for up to $725 for two ounces.
A few blocks from the harbor, in the heart of the city, the Langham Hotel resides in what was once the Federal Reserve Bank of Boston, as is evidenced in the décor of Grana, the hotel’s dramatic main restaurant and in the lobby. The elegant property is also decorated with 268 works of art, some from the owner’s private collection. For extra room to spread out, consider the property’s unique, bi-level suites with a king bed on the upper level and a sofa on the main level. Retreat from city streets with a workout in the well equipped fitness center, or unwind in the heated indoor pool, whirlpool or saunas. After a day of sightseeing on your Boston autumn getaway, sample cocktails and cuisine in the British-inspired cocktail bar, the Fed, where offerings take on a New England influence.
For more information on shoulder season in Boston and beyond, visit Meet Boston at www.meetboston.com or call 888-SEE-BOSTON.
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