Boston Off the Beaten Path: Cheap & Hidden Gems

Planning a trip to Boston? Want to avoid the tourists and experience Boston as a local?

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Beyond the Freedom Trail, Faneuil Hall and Harvard Square, there is so much more to discover in Boston than the typical tourist destinations. In this blog post, we share insider tips for cheap things to do, and take you on a journey to some of Boston’s most undiscovered places.

Boston City boston-beacon-hill

  1. Enjoy a 360-Degree View of Boston

Many visitors know about Boston’s Skywalk Observatory, offering a spectacular 360-degree view of the city. However, few people realize you can enjoy the same view for half the price (or for a more luxurious experience) if you visit the restaurant, Top of the Hub, located two floors above the Observatory. Order a drink or small snack and enjoy the Boston skyline from the 52nd floor of the Prudential Building.

Photo Credit: Boston Spotlite
Photo Credit: Boston Spotlite
  1. Walk or Bike the Minuteman Bikeway

“The bike path,” as it’s known by locals, passes through the historic area where the American Revolution began in April 1775. It connects the Alewife T station in Cambridge to nearby towns including Somerville and Lexington, and is meant to serve as an environmentally-friendly commuting option.

The bikeway has become a new type of Main Street where neighbors and strangers alike come together while riding, walking, or skating on the path.” – MassBike

Boston Minuteman Bikeway 2 Boston Minuteman Bikeway

  1. Grab a Seat Cushion and Relax in the Middle of Boston’s Financial District

During the summer, Norman B. Levanthal Park at Post Office Square is hugely popular among young professionals who work in the Financial District. The park provides complimentary seat cushions, free fitness classes, and local music ensembles. Our absolute favorite coffee shop in Boston, Sip Cafe, is also located in the park and housed in an almost completely glass building. If you like to support owner-operated business serving rich, smooth espresso drinks, you cannot miss this place.

Boston Norman Levanthal Park 2

Photo Credit: Street Pianos
Photo Credit: Street Pianos
  1. Play Bocce in Boston’s North End

For those who love the popular sport of Italian bowling, visit Langone Park in the North End of Boston, where you will find three regulation bocce courts. Grab a cannoli at Modern (one of the best North End bakeries) and immerse yourself in an Italian experience.

Boston Langone Park Bocce Ball

  1. Watch the Sun Set over the Boston Skyline

Order a Rowes Wharf water taxi ($10) from the Long Wharf to Hyatt Boston Harbor Hotel, and enjoy a spectacular view of Boston Harbor from the hotel patio as you sip a mojito or coffee, feel the ocean breeze, and watch the sun set over the city.

Credit: Boston Hyatt
Photo Credit: Boston Hyatt
  1. Check out a New England Conservatory Performance

A world-famous music school right around the corner from the Boston Symphony, the New England Conservatory is often overlooked by tourists but well-known among local musicians. Their performances, recitals, and chamber group concerts are often free.

 Boston New England Conservatory

  1. Sail the Charles

Visit the Community Boating building and leave a note with your name, phone number, and interest in learning how to sail. Someone will surely call you with an offer to join them on their boat.  Do not miss a chance to experience Boston from the Charles River.

Boston Sailing Charles River

  1. Shakespeare on the Common

Grab a blanket and experience America’s oldest park during a magical evening of free Shakespeare performances. A summertime tradition since 1996, Shakespeare on the Common run by the Commonweath Shakespeare Company is one of the most popular Boston theater events of the year.

Boston Shakespeare on the Common

  1. Climb Washington Tower at Mount Auburn Cemetery

The oldest rural cemetery in the US, Mount Auburn Cemetery is a beautiful retreat from the bustling city, and a great place to take in some of New England’s nature. If you’re visiting Boston during autumn, Mount Auburn’s collection of over 5,500 trees includes nearly 700 species and varieties offer a brilliant display of colors and fall foliage. Climb Washington Tower and get a panoramic view of Boston and nearby Cambridge.

Boston Mt Auburn Cemetery Boston Foliage

Boston Mt Auburn Cemetery Washington Tower

Have you visited any of these locations? Tell us what you think.