The Oregon Trail: Exploring Boston, Massachusetts

In the nearly 400 years since its founding, Boston (pop. 694,583) has witnessed more historically significant events than any American city even twice its size. The youthful energy of the city’s many college students certainly helps cloak its traditional Puritan parochialism, while the high-tech economic boom and the breaking of the “Curse of the Bambino” by the 2004 World Series-champion Boston Red Sox baseball team have helped loosen up a city previously best known for baked beans and banning sexy books.

There are lots of places to start a Boston tour, but a personal favorite is the Old North Church (193 Salem St., 617/523-6676, daily, $8), a Boston landmark since well before Paul Revere set off on his midnight ride. The steeple has been rebuilt, but almost everything else dates back to colonial times. The Paul Revere House (19 North Square, 617/523-2338, daily Apr.-Dec., Tues.-Sun. Jan.-Mar., $5), the oldest in Boston, is a few blocks away. The surrounding neighborhood, the predominantly Italian North End, is the city’s oldest and most pedestrian-friendly quarter. Its narrow streets jut out toward Boston harbor.

With its abundance of universities, museums, and cultural centers, Boston is packed with places to improve your mind. One of the nicest has to be the Isabella Stuart Gardner Museum (25 Evans Way, 617/566-1401, Wed.-Mon., $15). In the late 19th century, “Mrs. Jack” Gardner built her home in the style of a Venetian palazzo, crammed it with exquisite art, and then opened it as a museum. And what a museum, now better than ever thanks to the copper-and-glass Renzo Piano-designed addition fronting the lushly landscaped interior courtyard. (Note: Anyone named “Isabella” gets in free!) The much bigger Museum of Fine Arts (465 Huntington Ave., 617/267-9300, daily, $25) is only a short walk away and has more than 200 world-class galleries of just about every type and era of fine art, including world-class Impressionists and perhaps the best Japanese art collection in the United States.

For baseball fans, Boston’s must-see is Fenway Park (4 Yawkey Way, tickets 877/733-7699), home of the Red Sox. Located off Boylston Street, this is the oldest, smallest, and arguably most entertaining stadium in the nation.

Travel to Boston

Boston, a.k.a. “The Hub,” sits spider-like at the center of a web of major highways. Air travelers get to deal with the chaos and malfunction of Logan International Airport, the major gateway to New England for U.S. and overseas flights. Logan is central—just a seven-minute ride across Boston Harbor to downtown if you take the Water Shuttle. Logan is also connected to the city by the Blue Line subway run by Massachusetts Bay Transportation Authority (800/392-6100 or 617/222-3200), the “T,” a well-run and nearly comprehensive network of subways, buses, trams, ferries, and commuter trains. Despite the completion of the $15 billion Big Dig, Boston’s 21st-century traffic and 17th-century streets are not for faint-hearted drivers. Narrow, often unidentified, poorly maintained, and laid out in irregular patterns conforming to long-buried topography, the streets of Boston are also home to aggressive bumper-riding red light-runners. So park your car, take public transit, and walk.

Hotels and Restaurants in Boston

While nightly rates at top-end hotels run well over $400 a night, places to stay in Boston start with the budget HI-Boston Hostel (19 Stuart St., 617/536-9455, $44 per person, higher for a private room). As befitting a historical city such as Boston, the hostel is in a National Register of Historic Places building; as befitting the times, it is a green LEED-certified building as well. For a moderate price and a great location, right at the Copley Square finish line of the Boston Marathon, try the popular Charlesmark Hotel (655 Boylston, 617/247-1212, around $189 and up).

Thanks no doubt to Boston’s Puritan past, the city has never had a great reputation for its food, but things have definitely changed. For an old-fashioned Boston meal, you could go to Durgin-Park (617/227-2038, daily), open since 1827 in what’s now Faneuil Hall Market Place, or opt for the casual and popular James Hook & Company (15 Northern Ave., 617/423-5501), serving up delicious lobster rolls on the downtown waterfront since the 1920s. Boston also has more than a few great Mexican, Japanese, and Chinese places. For another only-in-Boston experience, head to The Daily Catch (323 Hanover St., 617/523-8567, daily, cash only), in the old North End within walking distance of the Haymarket T. This family-run place, started in 1973, is so tiny that the cook could shake hands with half his customers without leaving his stove. Calamari (squid) is the house specialty, but the menu’s mainstay is Sicilian seafood over linguine (with red or white sauce), served in sauté pans instead of on plates. It doesn’t take reservations, so expect a wait after 6pm.