| Mt Ascutney via Weathersfield Trail | Mount Ascutney | 4.8 mi | 2,054 ft | Hard |
| Black Swamp Trail and Shrewsbury Peak Trail Loop | Killington | 5.3 mi | 1,577 ft | Hard |
| Little Killington via Shrewsbury Peak Trail | Killington | 8.3 mi | 2,075 ft | Strenuous |
| Mt Ascutney via Brownsville Trail | Mount Ascutney | 5.3 mi | 2,366 ft | Strenuous |
| Mt Ascutney via Windsor Trail | Mount Ascutney | 5 mi | 2,479 ft | Strenuous |
| Killington Peak via Bucklin Trail | Killington | 7.5 mi | 2,457 ft | Strenuous |
| Pico Peak via Bucklin Trail | Killington | 7.3 mi | 2,066 ft | Strenuous |
| Appalachian Trail and Sherburne Pass Trail Loop | Killington | 9.1 mi | 2,440 ft | Strenuous |
| Pico Peak via Appalachian Trail | Killington | 8.5 mi | 2,180 ft | Strenuous |
| Lookout Rock via Summit Trail (Blue) | Manchester | 5.7 mi | 2,669 ft | Strenuous |
| Baker Peak via Lake Trail | Bromley & Stratton | 6.6 mi | 2,110 ft | Strenuous |
| Shrewsbury Peak via Black Swamp Trail | Killington | 4.3 mi | 1,281 ft | Hard |
| Appalachian Trail and Bucklin Trail Loop | Killington | 7.2 mi | 2,251 ft | Strenuous |
| Pico Peak via Sherburne Pass Trail | Killington | 5.2 mi | 1,695 ft | Hard |
| Prospect Rock Loop via Appalachian Trail | Bromley & Stratton | 8.3 mi | 1,711 ft | Strenuous |
| Peru Peak via Appalachian Trail | Bromley & Stratton | 5.9 mi | 1,213 ft | Hard |
| Bromley Mountain via Appalachian Trail | Bromley & Stratton | 5.5 mi | 1,419 ft | Hard |
| Blue Ridge Mountain via Canty Trail (Blue) | Killington | 4.5 mi | 1,411 ft | Hard |
| Killington Peak via Appalachian Trail | Killington | 8.5 mi | 2,409 ft | Strenuous |
| Shrewsbury Peak via Appalachian Trail | Killington | 8.6 mi | 2,229 ft | Strenuous |
| Green Mountain via Homer Stone Trail | Killington | 6.5 mi | 1,787 ft | Strenuous |
| Appalachian Trail and Green Mountain Trail Loop | Bromley & Stratton | 6.9 mi | 1,124 ft | Hard |
| Bear Mountain via Appalachian Trail | Killington | 8.7 mi | 1,666 ft | Strenuous |
| Peru Peak via Lake Trail | Bromley & Stratton | 10.3 mi | 2,764 ft | Strenuous |
| Spruce Peak via Appalachian Trail | Bromley & Stratton | 7.9 mi | 1,381 ft | Hard |
| Spruce Peak Loop via Appalachian Trail | Bromley & Stratton | 6.1 mi | 1,332 ft | Hard |
| Ludlow Mountain via Healdville Trail | Killington | 5.9 mi | 1,910 ft | Hard |
| Green Mountain via Appalachian Trail | Bromley & Stratton | 6.4 mi | 975 ft | Hard |
| Appalachian Trail and Shrewsbury Peak Trail Loop | Killington | 10.4 mi | 2,988 ft | Strenuous |
| Peru Peak via Old Job Trail | Bromley & Stratton | 10.3 mi | 1,621 ft | Strenuous |
| Baker Peak via Appalachian Trail | Bromley & Stratton | 8.3 mi | 1,384 ft | Strenuous |
| The Gallop Loop via Barton Trail | Manchester | 3.3 mi | 782 ft | Moderate |
| Green Mountain Trail | Bromley & Stratton | 6.4 mi | 1,075 ft | Hard |
| Bald Mountain via Aitken State Forest Trail | Killington | 2.7 mi | 708 ft | Moderate |
| Antone Mountain via McCormick Trail | Manchester | 7.6 mi | 1,753 ft | Strenuous |
| Neals Hill Loop via Wright Farm Trail | Upper Valley | 2.1 mi | 397 ft | Easy |
| Ascutney South via Bicentennial Trail | Mount Ascutney | 6.7 mi | 2,020 ft | Strenuous |
| Russell Hill via Catamount Side Trail | Killington | 2.6 mi | 481 ft | Moderate |
| Russell Hill via Black Swamp Trail | Killington | 4.8 mi | 522 ft | Moderate |
| Mt Ascutney via Futures Trail | Mount Ascutney | 2.7 mi | 1,128 ft | Moderate |
| Peru Peak via Griffith Lake Trail | Bromley & Stratton | 8.3 mi | 911 ft | Hard |
| Pinnacle via Appalachian Trail | Upper Valley | 3.3 mi | 950 ft | Moderate |
| Deer Leap Mountain via Deer Leap Trail (Blue) | Killington | 2.4 mi | 687 ft | Moderate |
| Deer Leap Rock via Appalachian Trail | Killington | 3.1 mi | 899 ft | Moderate |
| Owls Head via Gilberts Lookout (Blue) | Manchester | 2.8 mi | 1,170 ft | Moderate |
| Slack Hill Trail | Killington | 2.3 mi | 429 ft | Easy |
| Slab Trail and Summit Trail Loop | Mount Ascutney | 1.4 mi | 309 ft | Easy |
| Irene Falls Loop via Bucklin Trail | Killington | 6.9 mi | 2,082 ft | Strenuous |
| The Lookout via Appalachian Trail | Upper Valley | 4.8 mi | 954 ft | Moderate |
| Windmill Mountain via Jamie Latham Trail | Brattleboro | 4.1 mi | 428 ft | Moderate |
| Windmill Mountain via Holden Trail | Brattleboro | 2.8 mi | 461 ft | Moderate |
| Deer Knoll via Trout Lily Trail (White Purple) | Manchester | 2.4 mi | 558 ft | Moderate |
| Breakneck Hill via Appalachian Trail | Upper Valley | 3.1 mi | 447 ft | Moderate |
| Thistle Hill via Appalachian Trail | Upper Valley | 3.2 mi | 672 ft | Moderate |
| Appalachian Trail and Old Job Trail Loop | Bromley & Stratton | 10.1 mi | 1,231 ft | Strenuous |
| Baker Peak via Griffith Lake Trail | Bromley & Stratton | 9.1 mi | 396 ft | Moderate |
| Dana Hill via Appalachian Trail | Upper Valley | 2.5 mi | 714 ft | Moderate |
| Windmill Mountain via Townline Trail | Brattleboro | 3.8 mi | 909 ft | Moderate |
| Windmill Mountain via Cascade Trail | Brattleboro | 2.7 mi | 944 ft | Moderate |
| Windmill Mountain via Radford-Smith Trail | Brattleboro | 3.7 mi | 983 ft | Moderate |
| Bissell Hill via Shrewsbury Peak Trail | Killington | 4 mi | 577 ft | Moderate |
| Mt Ascutney via Summit Trail | Mount Ascutney | 1.3 mi | 309 ft | Easy |
| Deer Leap Rock via Deer Leap Trail (Blue) | Killington | 2.5 mi | 600 ft | Moderate |
| Haystack mountain trail (2.3 mi) | Manchester | 2.3 mi | 831 ft | Moderate |
| Little Rock Pond via Appalachian Trail | Killington | 11.2 mi | 1,612 ft | Strenuous |
| Russell Hill via Shrewsbury Peak Trail | Killington | 1.2 mi | 195 ft | Easy |
| Bemis Hill Loop via Hemlock Trail | Brattleboro | 3.2 mi | 484 ft | Moderate |
| Neals Hill via Pine Drop | Upper Valley | 3.6 mi | 581 ft | Moderate |
| Brownsville Trail and Norcross Trail Loop | Mount Ascutney | 7.5 mi | 2,893 ft | Strenuous |
| Norcross Trail and Windsor Trail Loop | Mount Ascutney | 7.1 mi | 2,656 ft | Strenuous |
| Bemis Hill via Athens Access Path | Brattleboro | 1.9 mi | 657 ft | Easy |
| Stratton Mountain via Stratton Ridge Trail | Bromley & Stratton | 1.2 mi | 102 ft | Easy |
| Little Mud Pond via Appalachian Trail | Bromley & Stratton | 7.8 mi | 1,228 ft | Hard |
| Stratton Pond via Appalachian Trail | Bromley & Stratton | 6.8 mi | 357 ft | Moderate |
| Neals Hill via Wright Farm Trail | Upper Valley | 1.4 mi | 211 ft | Easy |
| Hurricane Hill Loop via Beacon Hill Loop | Upper Valley | 1 mi | 208 ft | Easy |
| Spring Lake via Appalachian Trail | Killington | 7.7 mi | 1,014 ft | Hard |
| Mount Peg Loop via Constant Flow | Upper Valley | 1.1 mi | 234 ft | Easy |
| Muddy Pond Loop via Carriage Trail | Killington | 4.2 mi | 509 ft | Moderate |
| Bemis Hill via Hemlock Trail | Brattleboro | 3 mi | 240 ft | Easy |
| Lye Brook Falls via Lye Brook Trail | Bromley & Stratton | 4.5 mi | 857 ft | Moderate |
| Biscuit Hill via Bourdon Road | Upper Valley | 3.3 mi | 670 ft | Moderate |
| Hurricane Hill via Beacon Hill Loop | Upper Valley | 1.1 mi | 208 ft | Easy |
| Gerry's Falls via Windsor Trail | Mount Ascutney | 4 mi | 229 ft | Easy |
| Hidden Falls via Bicentennial Trail | Mount Ascutney | 5.3 mi | 242 ft | Moderate |
| Mount Peg via Dropout | Upper Valley | 1.1 mi | 234 ft | Easy |
| Muddy Pond via Carriage Trail | Killington | 3.9 mi | 376 ft | Moderate |
| Cort's Jester Loop | Mount Ascutney | 2.4 mi | 406 ft | Easy |
| Fletcher Hill via John Darling Road | Upper Valley | 3 mi | 297 ft | Easy |
| Biscuit Hill via Long Hill Road | Upper Valley | 3.1 mi | 113 ft | Easy |
| Blood Rock via Futures Trail | Mount Ascutney | 4.5 mi | 1,186 ft | Hard |
| Brownsville Trail | Mount Ascutney | 6.3 mi | 701 ft | Moderate |
| Biscuit Hill via Arhur Morgan Road | Upper Valley | 2.2 mi | 227 ft | Easy |
| Quarry Lookout via Norcross Trail | Mount Ascutney | 6.7 mi | 1,020 ft | Hard |
| Cold River Vista via Aitken State Forest Trail | Killington | 2.2 mi | 722 ft | Moderate |
| Neals Hill via Reservoir Road | Upper Valley | 2.7 mi | 226 ft | Easy |
| Little Cascade Falls via Weathersfield Trail | Mount Ascutney | 4.3 mi | 115 ft | Easy |
| Quarry Lookout via Brownsville Trail | Mount Ascutney | 3.7 mi | 229 ft | Easy |
| Beacon Hill Vista via Beacon Hill Loop | Upper Valley | 2.3 mi | 570 ft | Moderate |
| White Rocks via Appalachian Trail | Killington | 7.9 mi | 738 ft | Hard |
| Tinmouth Ridge Trail | Killington | 2.1 mi | 811 ft | Moderate |
| Delectable Mountain via Smith Hill Road | Upper Valley | 1.1 mi | 373 ft | Easy |
| Stony Brook Shelter via Appalachian Trail | Killington | 8.5 mi | 1,524 ft | Strenuous |
| Appalachian Trail from Thundering Brook Falls Trail | Killington | 3.2 mi | 424 ft | Moderate |
| Overlook | Killington | 2.9 mi | 406 ft | Easy |
| Hunker Down and Shale Shifter Loop | Manchester | 2.3 mi | 560 ft | Moderate |
| Hunker Down and Shale Shifter Loop and Porcupine | Manchester | 2.5 mi | 574 ft | Moderate |
| Viewpt Trail Loop | Manchester | 2 mi | 509 ft | Easy |
| Ice Bed Trail Loop | Killington | 1.7 mi | 355 ft | Easy |
| Ledges overlook trail Loop | Brattleboro | 1.4 mi | 641 ft | Easy |
| Beacon Hill Loop and Tower Trail | Upper Valley | 1.5 mi | 322 ft | Easy |
| Ice Bed Trail | Killington | 2 mi | 378 ft | Easy |
| Natural Bridge Falls via Dorset Hill Road | Bromley & Stratton | 3.7 mi | 391 ft | Moderate |
| Faulkner Trail | Upper Valley | 2.8 mi | 464 ft | Moderate |
| Hunker Down | Manchester | 2.1 mi | 560 ft | Easy |
| Shale Shifter | Manchester | 2.4 mi | 415 ft | Easy |
| Farm Trail | Manchester | 2 mi | 505 ft | Easy |
| Rolston Rest Shelter via Long Trail | Killington | 14.2 mi | 1,677 ft | Strenuous |
| Healdville Trail | Killington | 3 mi | 1,895 ft | Hard |
| Vista Trail (Blue) | Killington | 1 mi | 272 ft | Easy |
| Big Branch Shelter via Appalachian Trail | Bromley & Stratton | 9.1 mi | 518 ft | Moderate |
| Clarendon Shelter via Appalachian Trail | Killington | 2.2 mi | 587 ft | Moderate |
| Beacon Hill Vista via WB Brown Trail | Upper Valley | 1.1 mi | 153 ft | Easy |
| Lost Pond Shelter via Old Job Trail | Bromley & Stratton | 6.8 mi | 682 ft | Moderate |
| Governor Clement Shelter via Catamount Side Trail | Killington | 8 mi | 622 ft | Moderate |
| Log Shelter via Futures Trail | Mount Ascutney | 3.2 mi | 834 ft | Moderate |
| Bromley Shelter via Corridor 7 | Bromley & Stratton | 4.8 mi | 611 ft | Moderate |
| Pico Camp Shelter via Sherburne Pass Trail | Killington | 3.5 mi | 881 ft | Moderate |
| Tucker Johnson Shelter via Long Trail | Killington | 5.3 mi | 852 ft | Moderate |
| Ledges overlook trail | Brattleboro | 1.6 mi | 630 ft | Easy |
| Mt Moses Trail | Upper Valley | 4.2 mi | 735 ft | Moderate |
| Hemlock Trail (3.3 mi) | Brattleboro | 3.3 mi | 897 ft | Moderate |
| Appalachian Trail (6.8 mi) | Upper Valley | 6.8 mi | 1,156 ft | Hard |
| Old Job Shelter via Appalachian Trail | Bromley & Stratton | 4.6 mi | 211 ft | Easy |
| Churchill Scott Shelter via Appalachian Trail | Killington | 4.1 mi | 116 ft | Easy |
| Plymsbury Wildlife Management Area Trail | Killington | 2.9 mi | 343 ft | Easy |
| Slack Hill Trail (2.4 mi) | Killington | 2.4 mi | 224 ft | Easy |
| Ledges overlook trail (1.4 mi) | Brattleboro | 1.4 mi | 630 ft | Easy |
| Governor Clement Shelter via Appalachian Trail | Killington | 1.4 mi | 142 ft | Easy |
| Cloudland Shelter via Appalachian Trail | Upper Valley | 1.4 mi | 264 ft | Easy |
| Rich Trail | Mount Ascutney | 1.4 mi | 393 ft | Easy |
| Kent Brook Trail | Killington | 1 mi | 206 ft | Easy |