Running Package: On Your Mark…

Five sidewalk-skimming adventures to give the Esplanade a run for its money.
Illustrations by Jameson Simpson

The Proud Bostonian Run
Boston (About 3 miles)

This is the route to show an out-of-towner how things are, and always have been, in the Hub. Start in North Square in the North End, at number 19, which is 1. Paul Revere’s house. Head south on North Street, across the Greenway, and up into historic 2. Faneuil Hall. The tourists will make things difficult here, but zigzagging through their blobby masses can provide a cardio boost. Continue on to Government Center—apologizing for the eyesore that is City Hall—and turn left onto Tremont Street. After paying respects to the 3. Omni Parker House, home of the Boston cream pie, go right on Beacon Street, and follow it past the State House and the Shaw Memorial, dedicated to the all-African-American Massachusetts 54th Regiment. Stay the course to Kenmore Square, passing the original Cheers, a.k.a. the Bull & Finch. From Kenmore, cut up Brookline Avenue, and there she is: 4. Fenway Park, the Bostonian’s cathedral.

The Literary Landmarks Run

Concord (About 4 miles)

A helping of culture with that lung-bursting, thigh-burning jog? No problem. This bookish workout starts in the town’s Monument Square. Head southeast on Lexington Road, past the austere 1. Ralph Waldo Emerson House, where the godfather of Transcendentalism wrote his most famous essays. Farther down, on the left, is Orchard House, Louisa May Alcott’s home and inspiration for Little Women. Still farther, at the intersection of Hawthorne Lane, is 2. the Wayside, a manse bought by novelist Nathaniel Hawthorne in 1852. How gorgeous is that wraparound porch? Veer left onto Old Bedford Road until the next big intersection, Bedford Street. Go left. Just before reaching town, detour into Sleepy Hollow Cemetery. Make your way up to 3. Authors Ridge, where one headstone stands out for its appropriate simplicity: Henry.

The Practice-for-HeartBreak-Hill Run 

Brookline (About 2 miles, but feels like 10)

1. Anna’s Taqueria sits on the corner of Summit Avenue and Beacon Street, just west of Coolidge Corner, providing ample tortilla-fueled motivation to make it to the top of Corey Hill. Starting at the corner, run west on Beacon for nearly a half mile. Look for a sign for 2. Summit Path, a 791-foot-high set of stairs to the top of Corey Hill and 3. Outlook Park’s unexpectedly grand views of Boston. Jog slowly down Summit to Beacon. Repeat the entire loop. Reach Anna’s. Order a super carnitas.

Go on to the next page for two more runs…