The hardest hikes in Massachusetts, by the numbers
Of the 52 trails in Massachusetts in our dataset, 9 (17 percent) rate strenuous or very strenuous on the gain-and-distance scale we use and run 3 to 30 miles with at least 1,500 ft of climb; all 9 are listed here, highest rating first.
South Taconic Trail leads with 4,397 ft of gain over 21.4 miles, 205 ft per mile, with a steepest pitch of 62 percent.
Across the 9, gain runs from 1,503 to 4,397 ft and distance from 5.8 miles to 21.6 miles; the median gain is 2,226 ft and the median distance 13.3 miles.
5 of the 9 are point-to-point routes; the rest are loop (3) or out-and-back (1).
| # | Trail | Miles | Gain (ft) | Ft per mile | Max grade | Elevation (ft) | Rating | Profile |
|---|---|---|---|---|---|---|---|---|
| 1 | South Taconic Trail | 21.4 | 4,397 | 205 | 62% | 734 to 2,303 | 433.8 | |
| 2 | Wapack TrailCentral Massachusetts | 21.6 | 3,788 | 175 | 37% | 1,228 to 2,261 | 404.5 | |
| 3 | Tully TrailCentral Massachusetts | 21.1 | 2,347 | 111 | 28% | 549 to 1,195 | 314.7 | |
| 4 | Mahican - Mohawk Trail Section 5: Charlemont to North AdamsThe Berkshires | 15.2 | 2,006 | 132 | 45% | 704 to 2,563 | 246.9 | |
| 5 | Northfield Mountain TrailsWestern Massachusetts | 11.3 | 1,913 | 169 | 38% | 279 to 1,090 | 207.9 | |
| 6 | Mahican - Mohawk Trail Section 4: Charlemont - Cold RiverWestern Massachusetts | 10.9 | 1,846 | 169 | 58% | 580 to 1,895 | 200.6 | |
| 7 | Taconic Skyline TrailThe Berkshires | 13.3 | 1,503 | 113 | 16% | 1,536 to 2,336 | 199.9 | |
| 8 | Mount Greylock Summit LoopThe Berkshires | 6.6 | 2,226 | 337 | 41% | 1,249 to 3,475 | 171.4 | |
| 9 | Bellows Pipe to Mount Greylock SummitThe Berkshires | 5.8 | 2,231 | 385 | 44% | 1,249 to 3,478 | 160.9 |
How this list is ranked
Rating = the square root of 2 x elevation gain (ft) x distance (miles), the gain-and-distance formula Shenandoah National Park publishes for its own trails. Bands: under 50 easiest, 50 to 100 moderate, 100 to 150 moderately strenuous, 150 to 200 strenuous, 200 and over very strenuous.
This list: band strenuous (150 to 200) or very strenuous (200 and over), 3 to 30 miles, at least 1,500 ft of gain, ordered by rating desc, gain per mile desc, capped at 25. The rating column is computed from the miles and gain printed in the same row, the numbers each trail page uses, so every row can be checked from the row itself. The rating says nothing about exposure, scrambling, altitude or conditions.
Only trails with a full page count, so "Massachusetts" here means the 52 trails in Massachusetts in our dataset, not every trail in Massachusetts.
Each trail page shows the full elevation profile behind these numbers and the same data drawn as a topographic print, made to order. Start with South Taconic Trail.
Hardest hikes elsewhere.
The same ranking for other states in our dataset.