Best Day in Boston: Revolutionaries, Gardens & Italian Pastries

Boston, MA

  • The Richardsonian Romanesque architecture of Trinity Church. Photo: Boston College University Libraries.
  • The reflection of Trinity Church in the glass facade of the Hancock.
  • Tributes to victims of the Boston Marathon bombing.
  • The Boston Marathon finish line in front of the Boston Public Library.
  • Alexander Hamilton gazes from his pedestal on the Commonwealth Avenue.
  • 1850–1920 photo of the statue of Alexander Hamilton. Photo: Boston Public Library.
  • General George Washington marches in the Boston Garden.
  • The bridge over the lagoon in the Boston Garden.
  • The Old State Church.
  • Paul Revere’s 1770 engraving "The Bloody Massacre Perpetrated in King Street."
  • The meeting space upstairs in Faneuil Hall.
  • The entrance to Faneuil Hall.
  • A chocolate chip ricotta cannoli from Mike's Pastry.
  • Ordering at the counter at Mike's Pastry.
  • The nave inside the Old North Church.
  • The realistic bust of George Washington.

2 hours and 30 minutes
1.5 mi
Guided by Adam
Adam Donahue


When friends come to Boston and ask for suggestions on what to see, this is the walk that I give them. There is no better way to experience the history, nature, food and fashion of the city. Come on a walk of five neighborhoods, from chic Newbury St, to the mansions of Commonwealth Ave, to the charm of the Boston Common, to the Colonial trappings of Fanieul Hall, to the culinary delights of the Italian district. We'll end where the Revolutionary War began. If you only have a few hours in Boston, this is the way to see the best of the best.

About Your Guide

Cheers for: Boston sports teams. Eats: Japanese food. Travels: constantly. Subservient to: ice cream. And my son, especially if both are involved. Perfect vacation: long walks on a beach or long walks on a golf course.

Go on this Sidewalk

Guide Points

  1. Trinity Church

    We begin our walk in Copley Square at one of the most iconic buildings in the city.

  2. Boston Marathon Finish Line

    The Boston Marathon is one of the most famous races in the world. Over 30,000 people from around the world come to compete every year.

  3. Commonwealth Avenue

    Perhaps one of Boston's most attractive streets, Commonwealth Avenue features a greenway that runs past classical revival, Art Nouveau, and…

  4. Boston Public Garden & the George Washington Statue

    A 22-foot tall statue of George Washington on horseback stands before you. Compared to Hamilton's statue, Washington's looks triumphant and…

  5. Boston Common & the Frog Pond

    Since 1634, the Boston Common has served as the city's main green space. Originally it was a mere cow pasture, but as the literal "tragedy …

  6. Old State House

    Welcome to the site of the Boston Massacre. Outside of the Old State House a mob of colonials in 1770 gathered to voice their frustrations …

  7. Faneuil Hall + Quincy Market

    Faneuil Hall served as a public meeting space (upstairs) and marketing (downstairs) when constructed in 1742. Many anti-British speeches we…

  8. Mike's Pastry - Boston

    Have you seen people carrying around a white box with blue writing, all bundled up in string? They happy campers came from Mike's Pastry.

  9. Paul Revere Mall

    This quiet courtyard is one of my favorite places in the North End. It is open yet secluded from the bustle of the action on the main stree…

  10. Old North Church

    In the late 18th century, the Old North Church stood as the tallest building in Boston - 174-feet tall. Due to its height and the loyalties…

About Sidewalk

Sidewalk is an app that provides free, guided walk experiences that can be created by anyone with stories to share about places they know and love.

The app navigates people through a neighborhood walk using GPS turn-by-turn directions, rich imagery and storytelling.