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OROKO City Guide | Top 10 things to do in and around Boston

There’s a lot to do in the tiny state of Massachusetts and Boston is a pivotal point for an exciting holiday. With the entire city booming with American spirit, it’s easy to immerse yourself in Bostonian culture – whether it’s catching the sea breeze along the coast, slurping clam chowder or unravelling the events of America’s Revolutionary War. Here are the top things to do in and around the capital for a truly New England experience.

Take a day trip to Salem

Once the town of the chilling witch trials, Salem is the Halloween hub of the US and is just a 45-minute drive from Boston. Engage in spooky activities like viewing life-like scenes inside the Salem Witch Museum or creeping through the eerie Witch House - the only known building connected to the witch trial tragedies in 1693. Should you become exhausted from the gloom and fright, Salem offers plenty of cool spots along the coast, and even a tour of The House of Seven Gables, once home to the famous American novelist, Nathanial Hawthorne.

Walk the Freedom Trail

This is probably the number one thing to do in Boston – mostly because it has everything to do in Boston! If you’re struggling to decide what to see first, the freedom trail is a perfect place to start. There are two and half miles of sixteen historical landmarks, some of which are the oldest in this rather new country. Popular spots along the trail are the beautiful Boston Common, the Old Corner Bookstore, the Paul Revere House, and the USS Constitution. We recommend exploring the trail through a guided tour or a food and beer crawl.

Sail on a whale watching cruise

Boston Harbour cruises offers pure fun on the high seas. Spend the day spotting the majestic humpback whale, gawking at seabirds and watching dolphins dip in and out of the water. Whales are spotted so frequently that Boston naturalists have given them names! Sailing on one of the US’ biggest and fastest vessels is a brilliant way to observe these magnificent creatures within the comfort of the city limits.

Travel through time at Plimouth Plantation

Just a 45-min drive from Boston, Plimouth Plantation is a real-life replica of the village settled by the pilgrims in 1624. This engaging museum experience consists of dedicated actors with a story to tell, an impressive replica of the Mayflower, a reproduction of a Native American village, and even an authentic Thanksgiving dinner in November!

Eat oysters at the Ye Olde Union Oyster House

Set along the Freedom Trail is the Ye Olde Union Oyster House, the oldest restaurant in Boston and the oldest continually operating restaurant in the US. Customers have been pouring ales and slurping oysters in the facility since 1826. The restaurant has also achieved many milestones in its same period-pub-style architecture, like hiring America’s first ever waitress, Rose Carey, in the 1920s. We recommend at least sticking your head in - or stopping by for satisfying pub fare.

Take an architecture tour at the Boston Public Library

Out of all of Boston’s libraries, go to the one on Boylston Street, where the books aren’t the only things to check out. With its Renaissance-style architecture and its vast collection of over 20 million items, this library is a notable landmark in the grand scheme of Boston destinations. This library offers public and private tours daily, and even includes a few cafes for light bites. We recommend a guided tour or just browsing inside the illustrious Reading Room in the McKim Building.

Spend a day relaxing at Martha’s Vineyard

Martha’s Vineyard is made up of six towns stretching 100 square miles and is seven miles off the coast of Cape Cod. Just a 45-minute ferry ride from the mainland, Martha’s is known for its gorgeous, New England beaches with Vineyard Haven, Oak Bluffs and Edgartown being the most accessible for the public. Cruise to multiple beaches with a one-day bus pass, eat fresh seafood at the nearest clam shack, then perhaps end the day at a five-star restaurant, sipping a local red.

Take the ‘Hahvahd Tour’ at Harvard University

Harvard is one the oldest institutions of higher education in the States and has consistently been one of the most prestigious schools in the world. Spelled like the locals’ pronunciation, a tour from its students is the perfect way to see how it lives up to its name. The student led tour runs about 70 minutes and takes you through Harvard Yard, Memorial Hall, The Widener Library, Harvard Lampoon, and the John Harvard statue.

Take a pic, then grab a drink at Cheers Bar

Based on the hit 1980s television show, Cheers, the bar on Beacon Street is the real-life model that attracts travellers far and wide. Originally the Bull and Finch Pub, it became the real-life inspiration for the setting of Cheers the same year the bar was named ‘Best Neighbourhood Bar.’ Upon the success of the Cheers television show, the bar adopted the show’s name, and has been a popular picture spot for tv buffs and pop culture fanatics.

See the Boston Tea Party Ships & Museums

Voted the number one Patriotic Attraction in the US, the Boston Tea Party is a must-see for Americans, and a wonder for international visitors. This is a fun activity for anyone seeking an incredibly unique museum experience. Learn about this monumental moment in history through live actors, interactive exhibits, and full scale, 18th century replica ships. You can even throw your very own tea into the same waters used over 200 years ago.


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