Trail Races & Routes in Massachusetts
Explore 126 trail running and hiking routes across Massachusetts. 3 organized races and 123 training routes covering distances from 0.9 mi to 221.1 mi. Elevation gains range from 10 ft to 12,077 ft. View detailed terrain intelligence for every route.
Key Takeaways
Total Routes
126
Races / Routes
3 / 123
Distance Range
0.9 mi - 221.1 mi
Elevation Range
10 ft - 12,077 ft
Most Popular Distance
Other (79)
Surface Type
97% Trail
| Route Name | Location | Distance | Elevation Gain | Type | Race Date |
|---|---|---|---|---|---|
| Boston Marathon | Wellesley, Massachusetts | 26.2 mi | 613 ft | race | Apr 20, 2026 |
| Falmouth Road Race | Falmouth, Massachusetts | 7.1 mi | 189 ft | race | — |
| Cape Town Marathon | Manuel F. Correllus State Forest, Massachusetts | 27.0 mi | 684 ft | race | — |
| Virginia Wood Trail | Middlesex Fells Reservation, Massachusetts | 0.9 mi | 124 ft | route | — |
| Dark Hollow Pond Trail | Middlesex Fells Reservation, Massachusetts | 1.2 mi | 168 ft | route | — |
| Long Pond Nature Trail | Middlesex Fells Reservation, Massachusetts | 2.0 mi | 182 ft | route | — |
| Crystal Spring Trail | Middlesex Fells Reservation, Massachusetts | 2.4 mi | 265 ft | route | — |
| Groton Hills Trail | Groton, Massachusetts | 4.0 mi | 478 ft | route | — |
| Wharton Plantation Trail | Wharton Plantation, Massachusetts | 4.0 mi | 365 ft | route | — |
| Middlesex Canal Trail | Billerica, Massachusetts | 4.1 mi | 122 ft | route | — |
| ALC ACROSS Lexington Route C | Arlington's Great Meadows, Massachusetts | 4.1 mi | 245 ft | route | — |
| Maple Heights Farm | Westminster, Massachusetts | 4.2 mi | 632 ft | route | — |
| Rock Circuit Trail, Middlesex Fells (MA) | Middlesex County, Massachusetts | 4.2 mi | 508 ft | route | — |
| Indian Hill | Groton, Massachusetts | 4.3 mi | 668 ft | route | — |
| Around Muddy Pond | Muddy Pond Conservation Area, Massachusetts | 4.6 mi | 524 ft | route | — |
| Marion Stoddart Nashua River Loop | Groton, Massachusetts | 4.6 mi | 421 ft | route | — |
| Rock Circuit Trail | Middlesex Fells Reservation, Massachusetts | 4.6 mi | 366 ft | route | — |
| Crow Hill Ledges | Leominster State Forest, Massachusetts | 4.7 mi | 926 ft | route | — |
| Battle Road Trail | Minute Man National Historical Park, Massachusetts | 4.7 mi | 632 ft | route | — |
| Drumlin Hop | Groton, Massachusetts | 4.7 mi | 638 ft | route | — |
| Cross Fells Trail | Wright's Pond, Massachusetts | 4.7 mi | 445 ft | route | — |
| Nature Trail | Mohawk Trail State Forest, Massachusetts | 4.7 mi | 914 ft | route | — |
| Washington Mountain Marsh Trail | October Mountain State Forest, Massachusetts | 4.7 mi | 497 ft | route | — |
| Dunbar Brook Trail | Monroe State Forest, Massachusetts | 4.7 mi | 816 ft | route | — |
| BCT Section 7 Concord/Lincoln | Walden Pond State Reservation, Massachusetts | 5.1 mi | 431 ft | route | — |
| Royal Throne Trail | Groton, Massachusetts | 5.3 mi | 451 ft | route | — |
| ACROSS Lexington Route A | Lexington, Massachusetts | 5.5 mi | 438 ft | route | — |
| Walking City Trail Section 2 | Boston, Massachusetts | 5.5 mi | 503 ft | route | — |
| Town Forest Loop Trail | Groton, Massachusetts | 5.8 mi | 673 ft | route | — |
| Reservoir Trail | Middlesex Fells Reservation, Massachusetts | 5.9 mi | 500 ft | route | — |
| Walking City Trail Section 3 | Boston, Massachusetts | 6.0 mi | 555 ft | route | — |
| Reservoir Trail, Middlesex Fells (MA) | Middlesex County, Massachusetts | 6.1 mi | 430 ft | route | — |
| Mt. Misery via Fairhaven Trail | Middlesex County, Massachusetts | 6.2 mi | 502 ft | route | — |
| Mount Hunger Views | Ashburnham, Massachusetts | 6.3 mi | 812 ft | route | — |
| ALB ACROSS Lexington Route B | Lexington, Massachusetts | 6.7 mi | 413 ft | route | — |
| Agawam River Trail | Agawam, Massachusetts | 6.7 mi | 363 ft | route | — |
| Western Greenway | Waltham, Massachusetts | 6.9 mi | 804 ft | route | — |
| Skyline Trail, Middlesex Fells (MA) | Middlesex County, Massachusetts | 7.1 mi | 956 ft | route | — |
| Ken Cuddeback Trail | Amherst, Massachusetts | 7.1 mi | 423 ft | route | — |
| Walking City Trail Section 4 | Boston, Massachusetts | 7.5 mi | 354 ft | route | — |
| East Groton Tour | Groton, Massachusetts | 7.7 mi | 623 ft | route | — |
| Estabrook Concord-Carlisle | Estabrook Woods, Massachusetts | 7.9 mi | 433 ft | route | — |
| Thoreau’s Footsteps | Mount Greylock State Reservation, Massachusetts | 8.2 mi | 2,238 ft | route | — |
| Groton Town Forest Race 9.5 mile Loop | Groton, Massachusetts | 8.7 mi | 888 ft | route | — |
| Rounds Rock Trek | Mount Greylock State Reservation, Massachusetts | 8.8 mi | 1,181 ft | route | — |
| Blue Heron Trail (MA) | Norfolk County, Massachusetts | 8.9 mi | 161 ft | route | — |
| October Mountain Loop Trail | October Mountain State Forest, Massachusetts | 8.9 mi | 1,379 ft | route | — |
| Jones Nose to Summit | Mount Greylock State Reservation, Massachusetts | 9.1 mi | 2,425 ft | route | — |
| Freedom Trail | Boston, Massachusetts | 9.4 mi | 504 ft | route | — |
| Emerald Necklace | Suffolk County, Massachusetts | 9.5 mi | 269 ft | route | — |
| Minuteman Bikeway - multi-use rail trail (MA) | Middlesex County, Massachusetts | 10.1 mi | 199 ft | route | — |
| Shining Sea Bikeway (MA) | Barnstable County, Massachusetts | 10.7 mi | 108 ft | route | — |
| Walking City Trail Section 1 | Boston, Massachusetts | 10.7 mi | 763 ft | route | — |
| BCT 7 First Drumlin Route (LincolnWeston/Wayland) | Ogilvie Town Forest, Massachusetts | 10.8 mi | 552 ft | route | — |
| Rutland State Park and Barre Falls Loop (MA) | Worcester County, Massachusetts | 10.9 mi | 574 ft | route | — |
| Jeff Smith Trail | Pepperell, Massachusetts | 10.9 mi | 772 ft | route | — |
| Floodwater Triple Crown (MA) | Franklin County, Massachusetts | 11.0 mi | 2,443 ft | route | — |
| Wachusett Mtn (MA) | Worcester County, Massachusetts | 11.1 mi | 2,402 ft | route | — |
| South Groton Tour | Groton, Massachusetts | 11.2 mi | 1,115 ft | route | — |
| BCT 6 Acton/Concord | Concord, Massachusetts | 11.9 mi | 788 ft | route | — |
| Martha's Vineyard North Shore (MA) | Dukes County, Massachusetts | 11.9 mi | 317 ft | route | — |
| Mount Greylock Traverse | Cheshire, Massachusetts | 12.6 mi | 3,301 ft | route | — |
| Greylock AT Traverse (MA) | Berkshire County, Massachusetts | 12.6 mi | 3,301 ft | route | — |
| BCT 5a & 6 Billerica/Bedford/Concord | Bedford, Massachusetts | 12.8 mi | 710 ft | route | — |
| Wilbur’s Clearing to Summit | Mount Greylock State Reservation, Massachusetts | 13.0 mi | 3,087 ft | route | — |
| Mt Greylock, Thunderbolt Trail (MA) | Berkshire County, Massachusetts | 13.0 mi | 3,576 ft | route | — |
| BCT section 4 | Andover, Massachusetts | 13.4 mi | 1,342 ft | route | — |
| Upper Charles Trail (MA) | Middlesex County, Massachusetts | 13.4 mi | 100 ft | route | — |
| Skyline Trail | Middlesex Fells Reservation, Massachusetts | 13.6 mi | 707 ft | route | — |
| Western Greenway (MA) | Middlesex County, Massachusetts | 13.8 mi | 946 ft | route | — |
| Circuit Trail Bedford (Inner) | Bedford, Massachusetts | 13.9 mi | 636 ft | route | — |
| BCT 11 | Easton, Massachusetts | 14.1 mi | 607 ft | route | — |
| Worcester East-West Trail (MA) | Worcester County, Massachusetts | 14.1 mi | 1,615 ft | route | — |
| Coal Mine Brook Park > Cascades Park | Worcester, Massachusetts | 14.1 mi | 1,615 ft | route | — |
| Monoosnoc Ridge Trail (MA) | Worcester County, Massachusetts | 14.6 mi | 2,153 ft | route | — |
| Blue Hills Skyline Trail (MA) | Norfolk County, Massachusetts | 14.9 mi | 3,642 ft | route | — |
| Mount Toby Loop (MA) | Franklin County, Massachusetts | 15.2 mi | 2,625 ft | route | — |
| White Trail | Sherborn, Massachusetts | 15.6 mi | 820 ft | route | — |
| Andover Community Paths | Andover, Massachusetts | 15.7 mi | 696 ft | route | — |
| BCT 12 | East Bridgewater, Massachusetts | 15.8 mi | 645 ft | route | — |
| Groton Tour | Groton, Massachusetts | 16.3 mi | 1,574 ft | route | — |
| The Worcester seven hill round (MA) | Worcester County, Massachusetts | 17.0 mi | 1,830 ft | route | — |
| West Groton Tour | Groton, Massachusetts | 17.1 mi | 1,431 ft | route | — |
| Paul Revere's Midnight Ride (MA) | Middlesex County, Massachusetts | 17.4 mi | 668 ft | route | — |
| Plum Island - out and back (MA) | Essex County, Massachusetts | 17.5 mi | 10 ft | route | — |
| BCT 10 | Walpole, Massachusetts | 17.8 mi | 1,662 ft | route | — |
| Battle Road Trail (MA) | Middlesex County, Massachusetts | 18.9 mi | 498 ft | route | — |
| BCT 7 Lincoln/Wayland | Wayland, Massachusetts | 19.0 mi | 1,430 ft | route | — |
| Long 7 Sisters 22 (MA) | Hampshire County, Massachusetts | 19.7 mi | 5,696 ft | route | — |
| Whitehall Upton Loop (MA) | Middlesex County, Massachusetts | 20.2 mi | 1,490 ft | route | — |
| South Taconic Trail (NY, MA) | Berkshire County, Massachusetts | 20.8 mi | 4,757 ft | route | — |
| Norwottuck Rail Trail (MA) | Hampshire County, Massachusetts | 20.9 mi | 265 ft | route | — |
| Circuit Trail Bedford (Outer) | Bedford, Massachusetts | 21.1 mi | 1,569 ft | route | — |
| Tully Trail (MA) | Worcester County, Massachusetts | 22.0 mi | 2,707 ft | route | — |
| Southern New England Trunkline Trail (MA) | Worcester County, Massachusetts | 22.9 mi | 1,413 ft | route | — |
| Mount Greylock Round (MA) | Berkshire County, Massachusetts | 23.7 mi | 5,793 ft | route | — |
| Coast to coast trail Nantucket (MA) | Massachusetts | 24.5 mi | 548 ft | route | — |
| Nashua River Rail Trail (MA, NH) | Middlesex County, Massachusetts | 24.5 mi | 184 ft | route | — |
| Skyline Trail | Blue Hills Reservation, Massachusetts | 25.0 mi | 2,844 ft | route | — |
| BCT Section 13 | Hanson, Massachusetts | 25.5 mi | 1,117 ft | route | — |
| Cape Cod National Seashore Traverse (MA) | Barnstable County, Massachusetts | 25.5 mi | 2,824 ft | route | — |
| Ware River Rail Trail (MA) | Worcester County, Massachusetts | 25.6 mi | 551 ft | route | — |
| East-West Trail | Worcester, Massachusetts | 25.7 mi | 2,673 ft | route | — |
| Taconic Rim (MA, CT, NY) | Berkshire County, Massachusetts | 26.6 mi | 7,385 ft | route | — |
| Boston Walking City Trail (MA) | Suffolk County, Massachusetts | 27.4 mi | 1,342 ft | route | — |
| Cape Cod Rail Trail (MA) | Barnstable County, Massachusetts | 27.4 mi | 420 ft | route | — |
| Tour du Greylock (MA) | Berkshire County, Massachusetts | 28.4 mi | 7,395 ft | route | — |
| Hancock Shaker Village Loop (MA) | Berkshire County, Massachusetts | 28.6 mi | 5,727 ft | route | — |
| Pittsfield Loop | Pittsfield State Forest, Massachusetts | 28.6 mi | 5,727 ft | route | — |
| Trans Nantucket 3 Lighthouse Run (MA) | Massachusetts | 29.4 mi | 451 ft | route | — |
| Boroughs Loop (MA) | Middlesex County, Massachusetts | 30.8 mi | 2,310 ft | route | — |
| Malborough Loop | Marlborough, Massachusetts | 30.8 mi | 2,310 ft | route | — |
| The City on the Hills - Boston (MA) | Suffolk County, Massachusetts | 31.1 mi | 1,832 ft | route | — |
| Warner Trail (MA, RI) | Norfolk County, Massachusetts | 32.3 mi | 2,800 ft | route | — |
| Charles River Link Trail (MA) | Norfolk County, Massachusetts | 32.4 mi | 2,131 ft | route | — |
| Boston - City to Sea to Summit (MA) | Suffolk County, Massachusetts | 34.9 mi | 2,769 ft | route | — |
| ACROSS Lexington Challenge (MA) | Middlesex County, Massachusetts | 40.2 mi | 1,812 ft | route | — |
| Robert Frost Trail (MA) | Hampshire County, Massachusetts | 43.7 mi | 6,594 ft | route | — |
| Monadnock - Wachusett (NH, MA) | Worcester County, Massachusetts | 43.9 mi | 4,805 ft | route | — |
| State House to State House (MA, RI) | Norfolk County, Massachusetts | 50.0 mi | 1,204 ft | route | — |
| Cape Cod Run Against the Tides (MA) | Barnstable County, Massachusetts | 54.8 mi | 1,178 ft | route | — |
| Sky to Sky to Sky - Boston | Suffolk County, Massachusetts | 58.2 mi | 5,420 ft | route | — |
| Massachusetts Route 10 (MA) | Hampshire County, Massachusetts | 60.8 mi | 1,762 ft | route | — |
| Cape Cod Traverse (MA) | Massachusetts | 65.3 mi | 1,632 ft | route | — |
| Midstate Trail (MA) | Worcester County, Massachusetts | 90.5 mi | 7,060 ft | route | — |
| Bay Circuit Trail (MA) | Middlesex County, Massachusetts | 221.1 mi | 12,077 ft | route | — |
Frequently Asked Questions
How many trail races are in Massachusetts?
There are 3 organized races and 123 self-supported routes available in Massachusetts.
What is the average elevation gain in Massachusetts?
The average elevation gain is 1,603 feet, with routes ranging from 10 to 12,077 feet.
What distances are available in Massachusetts?
Available distances include: Marathon, 10K, 5K, Half Marathon, 50K, 50 Mile, 100K, 100 Mile, Ultra.
Can these trail routes in Massachusetts be used for hiking?
Yes. 97% of these routes are on trail surfaces, making them suitable for both trail running and hiking. The terrain analysis and elevation profiles help hikers plan their adventures just as effectively as runners.
What's the best time of year to run trails in Massachusetts?
Trail running conditions in Massachusetts vary by season and elevation. Check the race date column for organized events, which are typically scheduled during optimal weather windows. For year-round training routes, elevation profiles help you plan for seasonal conditions.
More Races in Massachusetts
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