​​​Boston Boundless Trail Section 1, Long Wharf North (Boston) to Savin Hill Beach (Boston)
Difficulty: 7.8 miles, with 279 feet of climbing that occurs at the middle and end of the section
Terrain: Paved paths, dirt paths, stairs, boardwalks, beach sands
Exposure: Partial sun and wind protection from trees and buildings, more exposure in the second half.

Boston Boundless Trail Section 2, Savin Hill Beach (Boston) to East Milton Square (Milton)
Difficulty: 7.8 miles, with 207 feet of climbing that’s broadly spread across the section
Terrain: Paved paths, dirt paths, stairs, wooden bridges
Exposure: Limited tree canopy coverage throughout the section, with most exposure on the coast

​Boston Boundless Trail Section 3, East Milton Square (Milton) to Blue Hills Trailside Museum (Milton)
Difficulty: T.K miles, with T,TKTK feet of climbing—the toughest section of the Boston Boundless Trail!
Terrain: Dirt paths, paved paths, stairs, rock slopes that may require scrambling, wooden bridges
Exposure: Lots of shade trees, with most sun and wind exposure limited to hilltops in the Blue Hills

​Boston Boundless Trail Section 4, Blue Hills Trailside Museum (Milton) to Riverdale Park (Dedham)
Difficulty: T.K. miles, with KTK feet of climbing that’s concentrated in the first half of the section
Terrain: Dirt paths, paved paths, stairs, wooden bridges
Exposure: Lots of shade trees, with most of the sun exposure limited to the west edge of the Blue Hills

Boston Boundless Trail Section 5, Riverdale Park (Dedham) to Waban Station (Newton)
Difficulty: T,K miles, with TKT feet of climbing that’s mostly spread across the section
Terrain: Dirt paths, paved paths, stairs, wooden bridges
Exposure: Periodic exposure to sun in the Cutler Park marshlands, but consistent shade otherwise

Boston Boundless Trail Section 6, Waban Station (Newton) to Oak Square (Boston)
Difficulty: 7.1 miles, with 433 feet of climbing that’s primarily in the second half of the section
Terrain: Dirt paths, paved paths, wooden bridges, stairs
Exposure: Lots of shade trees throughout the section, with periodic sun exposure in the Brighton area

Boston Boundless Trail Section 7, Oak Square (Boston) to Davis Square (Somerville)
Difficulty: 7.8 miles, with 92 feet of climbing—the flattest section of the Boston Boundless Trail!
Terrain: Paved paths, dirt paths, boardwalks, wooden bridges, stairs
Exposure: Frequent shade, with sun exposure in Watertown and between Fresh Pond and Blair Pond

Boston Boundless Trail Section 8, Davis Square (Somerville) to Bunker Hill Monument (Boston)
Difficulty: 5.8 miles, with 246 feet of climbing that’s mostly contained to the first half of the section
Terrain: Paved paths, dirt paths, stairs, boardwalks
Exposure: Regular sun protection from trees and buildings, with more exposure on the Charles River

Boston Boundless Trail Section 9, Bunker Hill Monument (Boston) to Chelsea Square (Chelsea)
Difficulty: 8.3 miles, with 256 feet of climbing that’s mostly at the beginning and end of the section
Terrain: Paved paths, dirt paths, stairs, boardwalks
Exposure: Occasional shade, with sun and wind exposure from the Mystic River to the Tobin Bridge

Boston Boundless Trail Section 10, Chelsea Square (Chelsea) to Revere Beach (Revere)
Difficulty: 5.3 miles, with 364 feet of climbing that’s broadly spread across the trail section
Terrain: Paved paths, dirt paths, stairs, wooden bridges
Exposure: Buildings and trees offer some buffering, with more sun and wind exposure toward Revere

Boston Boundless Trail Section 11, Revere Beach (Revere) to Beachmont Station (Revere)
Difficulty: 4.7 miles, with 302 feet of climbing throughout—the shortest Boston Boundless Trail section!
Terrain: Paved paths, dirt paths, stairs, boardwalks, beach sands
Exposure: Frequent sun and wind exposure, with some shade near Fort Heath Park and Belle Isle Marsh

Boston Boundless Trail Section 12, Beachmont Station (Revere) to Lewis Mall Wharf (Boston)
Difficulty: 6.6 miles, with 253 feet of climbing that mostly happens in the first half of the section
Terrain: Paved paths, dirt paths, stairs, boardwalks
Exposure: Intermittent shade from trees and buildings in a mostly sunnier and gustier part of Boston