Thanks to Boston’s long and dynamic history, it’s easy to assume that there’s no shortage of things to do for history buffs. But these little-known spots in the city prove that Boston is truly a destination with something for every traveler. Whether a traveler is looking for quirky details, rich cultural experiences, mouthwatering tastes, outdoor experiences, or world-class shopping, Boston is the ideal location for an autumn getaway. Find these hidden gems and local favorites to experience the city like a Bostonian this fall.
10 A Boston Bridge Measured In Smoots
The John Harvard Bridge has two local names: The Mass Ave. Bridge (short for Massachusets Avenue) and Smoot’s Bridge. The former name has a straightforward origin – the bridge connects with the major thoroughfare of the same name. The latter local nickname has a much more colorful explanation. As part of a fraternity pledge in 1958, an MIT student named Oliver Smoot was challenged to lay on the bridge and be measured head-to-foot across its length. Cheeky fraternity members marked Smoot’s height – five feet and seven inches – from one end of the bridge to the next. Those marks remain today, having been carefully maintained over the years and even retained after a major renovation.
9 Mike’s Pastry In The North End
The North End neighborhood is a traditionally Italian American community that has retained a wealth of restaurants, bakeries, and culture. Visitors to this neighborhood should take a scenic stroll down the winding brick sidewalks to enjoy the autumn weather. For the best cannoli in town, insiders swear by Mike’s Pastry. The popular handmade treats come in a variety of flavors and there is often a queue to order at the counter. There are many great options for dinner in this neighborhood, too, but it’s certainly understandable to have dessert first!
Newbury Street in the Back Bay Neighborhood is an ideal place for strolling and enjoying the crisp autumn weather. High-end retail shops flank both sides of the street, most in converted brick duplexes. Boston’s well-heeled residents come here to shop, and aspirational students from all over the city come here to window-shop. Visitors can take a break at any of the trendy coffee shops along the way. A visit to Newbury Comic’s flagship store is a must, to witness the playful chaos of the quirky, youthful comics shop.
7 The Theater District
Most travelers think of Boston as a historical city, but its contemporary spirit can’t be ignored. The Theater District near Boston Common, is the perfect place to take in the city’s vibrant theater scene. From off-broadway-style plays to major productions with big budgets, the variety of shows here is wide and ever-changing. Here, theater-lovers should plan an evening of fine dining in the city followed by the latest buzz-worthy show. It’s the perfect fall plan in Boston, as theater season begins at the height of autumn.
6 The First Lighthouse
New England is known for its lighthouses, but Little Brewster Lighthouse is the first in the country. Little Brewster Island is a very small island with a big history, but travelers often miss this important site. It’s been rebuilt since its first job of sending simple signal fires to seafarers in the early 18th century. To get up close, visitors should take a Boston Harbor Lighthouse Tour. The tour explains the long and important role the lighthouse has played in the country’s history, including its use during the Revolutionary War.
5 Orchard House: Architecture And Literature
Just outside of Boston, Orchard house is an essential attraction for bibliophiles and architecture buffs. This large but austere house is where American author Louisa May Alcott wrote Little Women in 1868. But the house has a larger historical value as well. When Alcott lived there with her parents and siblings, the house was already two hundred years old and had been home to multiple influential early Americans. The house itself is an exceptionally well-maintained example of pre-revolutionary architecture in New England and worth seeing on its own design merits.
4 Hollywood In Boston
Over the years, dozens of movies have been based in Boston. A self-guided film tour may take a little work to put together, but it is a rewarding way to see the city and both the hidden gems and iconic spots the city has to offer. But cinephiles don’t have to do any work putting together a tour these days. There are several silver screen tours available, from walking tours to bus routes. However, visitors who choose to indulge in the city’s cinematic history, will not be disappointed.
3 Downtown Crossing: Where Boston Blends
To feel the hustle and bustle of Boston, alight at the Downtown Crossing Street station. This area is frequented by Bostonians and tourists alike, and visitors will experience the city’s melting pot nature. Here, history mingles with modern life. The area is a shopper’s delight, too, featuring many mid-range and mass market stores with goodies for every budget. From here, it’s a short walk to other attractions like Boston Common, Chinatown, and the Financial District.
2 Dim Sum Brunch In China Town
Boston’s Chinatown is a traditionally Chinese American neighborhood and boasts a selection of grocery stores and restaurants catering to lovers of Chinese cuisine. To experience Chinatown like a local, visitors should enjoy a dim sum brunch at China Pearl Restaurant, one of the most popular dim sum restaurants in the city. There is usually a long queue made of the restaurant’s loyal regulars and local college students. When finally seated, guests can build their meals from a dizzying array of mall dishes served on wheeled carts pushed by efficient, no-nonsense waiters. The waiter will mark the order form for the table, to be tallied at the end of the meal. Enjoy the bottomless tea and energetic atmosphere of this charming family restaurant and Boston institution.
1 Jamaica Plain: Urban Oasis
Jamaica Plain, known locally (and affectionately) as JP, is a hidden gem that most travelers miss out on during trips to Boston. At the Stony Brook orange line station, visitors can alight in the energetic heart of this suburb. JP has a wealth of urban outdoor areas to explore. An afternoon spent walking Jamaica Pond in the height of fall foliage season is a quintessential Boston experience that’s not to be missed. The Pond is part of a network of parks in Boston known as the Emerald Necklace. Hyde Square, just nearby, offers charming local eateries serving delectable Latin American and Caribbean delights. It’s a truly local experience visitors won’t soon forget.