Favorite Routes Lists

15 Best Runs in Greater Boston

Boston is a fantastic running city, famous for the Marathon, paths along the Charles River, the Emerald Necklace, and the waterfront. Our selection of the 15 Best Runs in Greater Boston includes Boston proper, Metro West, (out to Rt. 495), the North Shore (to Newburyport near the New Hampshire border), and South Shore (toward the Cape).

For more nearby, see our guides to Cape Code & the Islands, Providence, Portsmouth, southern Maine, & more.


The Charles River Paths

Boston, MA

One of the most famous runs in the country. Run all the way from downtown to Newton! Sections on the Boston side and Cambridge side, with numerous bridges along the way, allowing for great loops.

The Emerald Necklace

Boston, MA

A greenway originally conceived by Frederick Law Olmsted, running 10 miles from the State House to Franklin Park. Highlights include the Comm. Ave Mall, Fens, Jamaica Pond, Arboretum, and Franklin Park.

Apple Orchard Runs

Fall Foliage Runs in Massachusetts

Three routes in the orchard towns of Harvard, Stow, and Bolton west of Boston around Rt. 495. Lovely roads, with fun hills and great views to orchards and the valley. 5 and 10 mile options from the Apple Harvest Ramble in Harvard, or a route along the new Assabet River Rail Trail.

Newburyport & Plum Island

Boston, MA - North Shore

Great coastal town with terrific running options: 4.5 miles along the water and marshes out to Plum Island; Clipper City Rail Trail; and Maudslay State Park, with miles of trails featuring 19th century gardens, rolling meadows, & towering pines.

Worlds End

Boston, MA - South Shore

Overlooking Hingham Harbor just south of Boston, Worlds End offers several miles of roads and trails, flanked by specimen trees, with great views to the water and the Boston skyline. Enjoy 3+ miles of carriage road type trails in this Olmsted-designed park.