The Insta-Worthy Stroll of Back Bay & Beacon Hill, Boston

Boston, MA

  • Acorn St from the top of the hill.
  • Bates Hall at the Boston Public Library.
  • The courtyard at the Boston Public Library. Photo: Carly Siegel.
  • The medieval styling of the Charles Amos Cummings House.
  • Queen Anne architecture in foreground, Romanesque in background. Photo: bobby_in_boston.
  • Commonwealth Ave in the early fall as the leaves begin to turn. Photo: borntotravel2.
  • Early spring morning on Commonwealth Ave. Photo: Haoidoit.
  • The bridge over the Boston Public Garden lagoon at dusk. Photo: Juergen Roth.
  • The insignia of the city on the Boston Gardens gate.
  • The decor at Tatte in Beacon Hill. Photo: cecilydlp.
  • Photo: a cup of chai and a breakfast sandwich at Tatte. Photo: karenxreyes.
  • Straight-on view of Acorn St after a rain. Photo: daniel_in_boston.
  • Acorn St from the bottom of the hill. Photo: becky_barrick.

1 hour
1.1 mi
Guided by Brie
Brie McAllister


There are places that make you work for a so-so photo and there are others that let you accidentally capture masterpieces. The Back Bay and Beacon Hill neighborhoods are more of the latter. This walk of photogenic Boston is filled with my favorite spots to photograph some of the most iconic vistas of the city. We'll explore a variety of places, from a magical library hall to medieval-inspired brick houses, from artisanal French pastries to Colonial-era cobblestone streets. Come photograph Boston in a new light - Instagram will go nuts.

About Your Guide

Fan of action flicks & rom coms, Chance the Rapper & Cage the Elephant, cupcakes & Thanksgiving stuffing. My mom says I'm all over the place, but I would say I'm just multi-talented.

Go on this Sidewalk

Guide Points

  1. Bates Hall @ Boston Public Library

    It may seem odd that we are head into the Public Library for pictures, but in a town with 35 universities and 150,000+ students, academia i…

  2. Charles Amos Cummings House

    Stand at the corner outside of H&M and look catty corner across the street. There is a killer view of a medieval-looking brick building tha…

  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. Suspension Bridge @ Boston Public Garden

    The Boston Public Garden boasts what was once the world's shortest functioning suspension bridge. It has since been converted into a girder…

  5. Tatte Bakery & Café

    Tatte Bakery is practically engineered for Instagram. Things to note:

  6. Acorn Street

    Beacon Hill was established in 1795 and the neighborhood does what it can to worship its roots.

Sidewalk Reviews

  1. 3 Reviews

    1. bbmurr87

    Oct 9, 2021

    1. Vladimir Ofitserov

    Jul 27, 2021

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.