| Adams Apple via Laura Cowles Trail | Stowe | 4.5 mi | 2,534 ft | Strenuous |
| Antone Mountain Loop via Wildlife Trail | Manchester | 6.4 mi | 1,596 ft | Hard |
| Appalachian Trail and Sherburne Pass Trail Loop | Killington | 9.1 mi | 2,440 ft | Strenuous |
| Bald Mountain Loop via Long Pond Trail | Northeast Kingdom | 7.2 mi | 2,145 ft | Strenuous |
| Battell Mountain via Long Trail | Breadloaf | 8.4 mi | 2,189 ft | Strenuous |
| Belvidere Mountain via Long Trail | Northern Long Trail | 4.9 mi | 2,071 ft | Hard |
| Black Swamp Trail and Shrewsbury Peak Trail Loop | Killington | 5.3 mi | 1,577 ft | Hard |
| Bolton Mountain via Long Trail | Stowe | 9.9 mi | 2,934 ft | Strenuous |
| Burrows Trail and Long Trail Loop | Camel's Hump | 5.1 mi | 2,382 ft | Strenuous |
| Camels Hump via Burrows Trail | Camel's Hump | 4.4 mi | 2,257 ft | Hard |
| Camels Hump via Monroe Trail | Worcester Range | 5.8 mi | 2,600 ft | Strenuous |
| Cliff Trail and Long Trail Loop | Stowe | 3.5 mi | 1,690 ft | Hard |
| Doll Peak via Long Trail | Northern Long Trail | 8.7 mi | 2,018 ft | Strenuous |
| Emily Proctor Trail and Long Trail Loop | Breadloaf | 13.4 mi | 3,596 ft | Strenuous |
| Forester's Trail and Frank Post Trail Loop | Northern Long Trail | 7.2 mi | 2,146 ft | Strenuous |
| Killington Peak via Bucklin Trail | Killington | 7.5 mi | 2,457 ft | Strenuous |
| Lincoln Peak via Battell Trail | Breadloaf | 6.6 mi | 2,608 ft | Strenuous |
| Little Killington via Shrewsbury Peak Trail | Killington | 8.3 mi | 2,075 ft | Strenuous |
| Lookout Rock via Summit Trail (Blue) | Manchester | 5.7 mi | 2,669 ft | Strenuous |
| Mount Ellen via Long Trail | Camel's Hump | 9.1 mi | 2,120 ft | Strenuous |
| Mount Ethan Allen via Monroe Trail | Worcester Range | 6.1 mi | 2,203 ft | Strenuous |
| Mount Mansfield via Hell Brook Trail | Stowe | 2.6 mi | 2,446 ft | Hard |
| Mount Mansfield via Long Trail | Stowe | 4.3 mi | 2,694 ft | Strenuous |
| Mount Putnam via Middlesex Trail | Worcester Range | 8.9 mi | 2,435 ft | Strenuous |
| Mount Putnam via Skyline Trail | Worcester Range | 7.4 mi | 2,762 ft | Strenuous |
| Mount Putnam via Stowe Pinnacle Trail | Worcester Range | 5.2 mi | 2,532 ft | Strenuous |
| Mount Wilson via Clark Brook Trail | Breadloaf | 7.6 mi | 2,524 ft | Strenuous |
| Mount Wilson via Emily Proctor Trail | Breadloaf | 7.5 mi | 2,137 ft | Strenuous |
| Mount Wilson via Skylight Pond Trail West | Breadloaf | 8.7 mi | 2,148 ft | Strenuous |
| Mt Ascutney via Brownsville Trail | Mount Ascutney | 5.3 mi | 2,366 ft | Strenuous |
| Mt Ascutney via Weathersfield Trail | Mount Ascutney | 4.8 mi | 2,054 ft | Hard |
| Mt Ascutney via Windsor Trail | Mount Ascutney | 5 mi | 2,479 ft | Strenuous |
| Pico Peak via Appalachian Trail | Killington | 8.5 mi | 2,180 ft | Strenuous |
| Pico Peak via Bucklin Trail | Killington | 7.3 mi | 2,066 ft | Strenuous |
| Stark Mountain via Jerusalem Trail | Breadloaf | 5.1 mi | 2,059 ft | Hard |
| White Rock Mountain via Waterbury Trail | Worcester Range | 5 mi | 2,214 ft | Hard |
| Whiteface Mountain via Beaver Meadow Trail | Stowe | 6.4 mi | 2,175 ft | Strenuous |
| Baker Peak via Lake Trail | Bromley & Stratton | 6.6 mi | 2,110 ft | Strenuous |
| Haystack Mountain via Long Trail | Northern Long Trail | 8.5 mi | 2,332 ft | Strenuous |
| Little Haystack Mountain Loop via Masters Mtn Trail | Manchester | 10 mi | 2,437 ft | Strenuous |
| Appalachian Trail and Bucklin Trail Loop | Killington | 7.2 mi | 2,251 ft | Strenuous |
| Fire Tower Trail and Ridge Trail Loop | Stowe | 3.9 mi | 1,224 ft | Moderate |
| Jay Peak via Long Trail | Northern Long Trail | 3 mi | 1,621 ft | Moderate |
| Mount Ethan Allen via Forest City Trail | Camel's Hump | 4.5 mi | 1,957 ft | Hard |
| Mount Grant via Cooley Glen Trail | Breadloaf | 7.9 mi | 1,987 ft | Strenuous |
| Mount Grant via Long Trail | Breadloaf | 8 mi | 1,468 ft | Strenuous |
| Mount Putnam via Hogback Trail | Worcester Range | 4.6 mi | 1,921 ft | Hard |
| Nancy Hanks Peak via Long Trail | Breadloaf | 7.1 mi | 1,800 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 |
| Shrewsbury Peak via Black Swamp Trail | Killington | 4.3 mi | 1,281 ft | Hard |
| Stratton Mountain via Appalachian Trail | Bromley & Stratton | 6.7 mi | 1,612 ft | Hard |
| The Forehead via Maple Ridge Trail | Stowe | 6.5 mi | 1,606 ft | Hard |
| Bald Mountain Trail | Bennington | 7.7 mi | 2,122 ft | Strenuous |
| Bald Mountain via Long Pond Trail | Northeast Kingdom | 4.1 mi | 1,430 ft | Hard |
| Bald Mountain via Mad Brook Trail | Northeast Kingdom | 5.4 mi | 1,497 ft | Hard |
| Belvidere Mountain via Forester's Trail | Northern Long Trail | 5.7 mi | 1,916 ft | Hard |
| Blue Ridge Mountain via Canty Trail (Blue) | Killington | 4.5 mi | 1,411 ft | Hard |
| Boyce Mountain via Skylight Pond Trail West | Breadloaf | 6.7 mi | 1,749 ft | Strenuous |
| Bromley Mountain via Appalachian Trail | Bromley & Stratton | 5.5 mi | 1,419 ft | Hard |
| Camels Hump via Long Trail | Camel's Hump | 10.3 mi | 3,875 ft | Strenuous |
| Cape Lookoff Mountain via Long Trail | Moosalamoo | 3.2 mi | 1,211 ft | Moderate |
| Morse Mountain via Beaver Meadow Trail | Stowe | 6.7 mi | 1,824 ft | Strenuous |
| Peru Peak via Appalachian Trail | Bromley & Stratton | 5.9 mi | 1,213 ft | Hard |
| Ricker Mountain via Cobrass Run | Worcester Range | 4.4 mi | 1,418 ft | Hard |
| White Rock Mountain via Middlesex Trail | Worcester Range | 4.7 mi | 1,571 ft | Hard |
| Worth Mountain via Long Trail | Breadloaf | 5.6 mi | 1,265 ft | Hard |
| Bluff Mountain via Bluff Ridge Trail | Northeast Kingdom | 8.3 mi | 1,824 ft | Strenuous |
| Burke Mountain Loop via Red Trail | Northeast Kingdom | 5.5 mi | 1,862 ft | Hard |
| Mount Carmel Loop via Long Trail | Moosalamoo | 8.8 mi | 1,928 ft | Strenuous |
| Woodward Mountain via Cobrass Run | Worcester Range | 4.1 mi | 1,294 ft | Hard |
| Antone Mountain via Wildlife Trail | Manchester | 6.1 mi | 1,240 ft | Hard |
| Carleton Mountain via Long Trail | Northern Long Trail | 5.2 mi | 1,313 ft | Hard |
| Elmore Mountain via Fire Tower Trail | Stowe | 3.1 mi | 1,229 ft | Moderate |
| Gore Mountain East Trail | Northeast Kingdom | 4.7 mi | 1,209 ft | Hard |
| Gore Mountain Trail | Northeast Kingdom | 7.7 mi | 1,976 ft | Strenuous |
| Green Mountain via Homer Stone Trail | Killington | 6.5 mi | 1,787 ft | Strenuous |
| Killington Peak via Appalachian Trail | Killington | 8.5 mi | 2,409 ft | Strenuous |
| Maple Hill via Appalachian Trail | Glastenbury | 4 mi | 1,321 ft | Hard |
| Mount Ethan Allen via Long Trail | Camel's Hump | 9.2 mi | 2,904 ft | Strenuous |
| Mount Hor via Moose Mountain Trail | Northeast Kingdom | 7 mi | 1,602 ft | Hard |
| Mount Hunger via Skyline Trail | Worcester Range | 9.6 mi | 2,838 ft | Strenuous |
| Mount Pisgah via North Trail | Northeast Kingdom | 4.3 mi | 1,511 ft | Hard |
| Mount Pisgah via South Trail | Northeast Kingdom | 3.5 mi | 1,462 ft | Hard |
| Shrewsbury Peak via Appalachian Trail | Killington | 8.6 mi | 2,229 ft | Strenuous |
| Whiteface Mountain via Long Trail | Stowe | 6.5 mi | 2,510 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 |
| Middle Mountain Trail | Northeast Kingdom | 6.1 mi | 1,558 ft | Hard |
| Mount Anthony via Summit Trail | Bennington | 2.3 mi | 1,238 ft | Moderate |
| Mount Moosalamoo Loop via Keewaydin Trail | Moosalamoo | 5.7 mi | 1,285 ft | Hard |
| The Forehead via Long Trail | Stowe | 10.5 mi | 2,947 ft | Strenuous |
| Dome Trail | Bennington | 5 mi | 1,700 ft | Hard |
| Domeys Dome via Long Trail | Northern Long Trail | 9.1 mi | 2,076 ft | Strenuous |
| Mount Norris Trail | Northern Long Trail | 3.7 mi | 1,345 ft | Moderate |
| 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 |
| Stimson Mountain via Long Trail | Camel's Hump | 3.5 mi | 1,210 ft | Moderate |
| Ernie's Trail and Writghts Mountain Trail Loop | Groton | 3.5 mi | 956 ft | Moderate |
| Perry Hill Loop via Rasta Man | Worcester Range | 5.3 mi | 1,136 ft | Hard |
| Putney Mountain via West Cliff Trail | Brattleboro | 5.6 mi | 1,435 ft | Hard |
| Spruce Peak Loop via Appalachian Trail | Bromley & Stratton | 6.1 mi | 1,332 ft | Hard |
| Stimson Mountain Loop via Long Trail | Camel's Hump | 7.4 mi | 1,830 ft | Strenuous |
| Terrill Hill Loop via Tower Climb | Stowe | 3.2 mi | 703 ft | Moderate |
| Appalachian Trail and Shrewsbury Peak Trail Loop | Killington | 10.4 mi | 2,988 ft | Strenuous |
| Bald Top Loop via Cross Rivendell Trail | Groton | 5.7 mi | 1,561 ft | Hard |
| Burke Mountain via Red Trail | Northeast Kingdom | 4.4 mi | 1,838 ft | Hard |
| Glastenbury Mountain via Appalachian Trail | Glastenbury | 11.7 mi | 1,857 ft | Strenuous |
| Green Mountain via Appalachian Trail | Bromley & Stratton | 6.4 mi | 975 ft | Hard |
| Ludlow Mountain via Healdville Trail | Killington | 5.9 mi | 1,910 ft | Hard |
| Mount Carmel via Long Trail | Moosalamoo | 6.6 mi | 1,411 ft | Hard |
| Mount Pisgah via Long Pond Trail | Northeast Kingdom | 5 mi | 971 ft | Moderate |
| Ricker Mountain via Danger Pond | Worcester Range | 3.8 mi | 1,285 ft | Moderate |
| Stratton Mountain via Stratton Pond Trail | Bromley & Stratton | 12.8 mi | 1,924 ft | Strenuous |
| West Peak Burke Mountain via Red Trail | Northeast Kingdom | 3.7 mi | 1,703 ft | Hard |
| West Peak Burke Mountain via West Peak Trail | Northeast Kingdom | 6.9 mi | 1,575 ft | Hard |
| Baker Peak via Appalachian Trail | Bromley & Stratton | 8.3 mi | 1,384 ft | Strenuous |
| Big Rock Hill via Summit Loop Trail | Northeast Kingdom | 2.3 mi | 612 ft | Moderate |
| Harmon Hill via Appalachian Trail | Glastenbury | 7.7 mi | 661 ft | Hard |
| Hedgehog Mountain via North Trail | Northeast Kingdom | 5.5 mi | 903 ft | Moderate |
| Molly Stark Mountain via Beane Trail | Camel's Hump | 5.3 mi | 1,594 ft | Hard |
| Peru Peak via Old Job Trail | Bromley & Stratton | 10.3 mi | 1,621 ft | Strenuous |
| Rochester Mountain via Cassidy's Chase | Breadloaf | 3.9 mi | 1,210 ft | Moderate |
| The Gallop Loop via Barton Trail | Manchester | 3.3 mi | 782 ft | Moderate |
| Antone Mountain via Masters Mtn Trail | Manchester | 5.6 mi | 1,588 ft | Hard |
| Antone Mountain via McCormick Trail | Manchester | 7.6 mi | 1,753 ft | Strenuous |
| Bald Mountain via Aitken State Forest Trail | Killington | 2.7 mi | 708 ft | Moderate |
| Deer Mountain via Coldwater Brook Trail | Groton | 4.3 mi | 829 ft | Moderate |
| Devils Hill via Peacham Bog Loop | Groton | 9.8 mi | 985 ft | Hard |
| Green Mountain Trail | Bromley & Stratton | 6.4 mi | 1,075 ft | Hard |
| Irish Hill via Darling Road Trail | Groton | 3.5 mi | 1,003 ft | Moderate |
| Laraway Mountain via Long Trail | Northern Long Trail | 5.5 mi | 1,227 ft | Hard |
| Mount Hor via North Trail | Northeast Kingdom | 8.3 mi | 1,421 ft | Strenuous |
| Mount Worcester Trail | Worcester Range | 4.5 mi | 1,926 ft | Hard |
| The Gallop via Barton Trail | Manchester | 6.3 mi | 1,514 ft | Hard |
| Wrights Mountain via Writghts Mountain Trail | Groton | 3.1 mi | 914 ft | Moderate |
| Kew Hill Loop via Plum Line | Breadloaf | 5.1 mi | 868 ft | Moderate |
| Neals Hill Loop via Wright Farm Trail | Upper Valley | 2.1 mi | 397 ft | Easy |
| Paine Mountain via Unmaintained Hiking Trail | Worcester Range | 6.6 mi | 1,594 ft | Hard |
| Wheeler Mountain Trail | Northeast Kingdom | 4 mi | 977 ft | Moderate |
| Ascutney South via Bicentennial Trail | Mount Ascutney | 6.7 mi | 2,020 ft | Strenuous |
| Brigham Hill Loop via Indian Brook Loop Trail | Champlain Valley | 5.7 mi | 599 ft | Moderate |
| Burnt Rock Mountain via Catamount Trail | Camel's Hump | 12.1 mi | 2,376 ft | Strenuous |
| Dana Hill Loop via Evolution | Breadloaf | 3.5 mi | 679 ft | Moderate |
| Dome 2/3 Summit Trail | Bennington | 6.4 mi | 1,605 ft | Hard |
| Haystack Mountain via South Trail | Northeast Kingdom | 2 mi | 500 ft | Easy |
| Mount Carmel via New Boston Trail | Killington | 2.8 mi | 931 ft | Moderate |
| Mt Ascutney via Futures Trail | Mount Ascutney | 2.7 mi | 1,128 ft | Moderate |
| Paine Mountain Trail Loop | Groton | 4.6 mi | 1,188 ft | Hard |
| Perry Hill via Permission | Worcester Range | 4.5 mi | 928 ft | Moderate |
| Peru Peak via Griffith Lake Trail | Bromley & Stratton | 8.3 mi | 911 ft | Hard |
| Russell Hill via Black Swamp Trail | Killington | 4.8 mi | 522 ft | Moderate |
| Russell Hill via Catamount Side Trail | Killington | 2.6 mi | 481 ft | Moderate |
| Saxon Hill Loop via Mojo | Camel's Hump | 2 mi | 417 ft | Easy |
| Snake Mountain via East Trail | Breadloaf | 5 mi | 1,070 ft | Hard |
| Snake Mountain via Pond Summit Trail | Moosalamoo | 4 mi | 968 ft | Moderate |
| Terrill Hill via Tower Climb | Stowe | 3.1 mi | 678 ft | Moderate |
| Beane Mountain via Long Trail | Camel's Hump | 2.7 mi | 739 ft | Moderate |
| Hogback Mountain via Sucker Brook - Blueberry Hill Trail | Breadloaf | 5.3 mi | 254 ft | Moderate |
| Molly Stark Mountain via Catamount Trail | Camel's Hump | 12.8 mi | 2,245 ft | Strenuous |
| Molly Stark Mountain via Long Trail | Camel's Hump | 13.3 mi | 2,623 ft | Strenuous |
| Mount Clark via Long Trail | Stowe | 9.7 mi | 1,101 ft | Hard |
| Woodward Mountain via Danger Pond | Worcester Range | 3.6 mi | 1,170 ft | Moderate |
| Bearclaw and Loop Trail | Brattleboro | 1.9 mi | 290 ft | Easy |
| Chamberlain Hill Loop via Full House | Camel's Hump | 2.6 mi | 657 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 |
| Glastenbury Mountain via West Ridge Trail | Bennington | 17.5 mi | 3,149 ft | Strenuous |
| Haystack Mountain Trail | Glastenbury | 4 mi | 1,008 ft | Moderate |
| Mount Moosalamoo via Keewaydin Trail | Moosalamoo | 3.9 mi | 1,114 ft | Moderate |
| Owls Head via Gilberts Lookout (Blue) | Manchester | 2.8 mi | 1,170 ft | Moderate |
| Owlshead Mountain via Owls Head Trail | Groton | 3.4 mi | 349 ft | Easy |
| Pinnacle via Appalachian Trail | Upper Valley | 3.3 mi | 950 ft | Moderate |
| Dana Hill via Enchanted Forest Trail | Breadloaf | 3 mi | 278 ft | Easy |
| Deer Knoll via Summit Trail (Blue) | Manchester | 6.1 mi | 461 ft | Moderate |
| Deer Knoll via Trout Lily Trail (White Purple) | Manchester | 2.4 mi | 558 ft | Moderate |
| Lincoln Gap via Battell Trail | Breadloaf | 6.7 mi | 1,763 ft | Strenuous |
| Little Deer Mountain via Telephone Line Trail | Groton | 3.2 mi | 284 ft | Easy |
| Middlebury Gap via Long Trail | Breadloaf | 8.5 mi | 1,466 ft | Strenuous |
| Paine Mountain via Pony Express | Groton | 4 mi | 1,059 ft | Moderate |
| Skidoo Mountain via Twin Peaks Trail | Breadloaf | 4.9 mi | 1,665 ft | Hard |
| Slab Trail and Summit Trail Loop | Mount Ascutney | 1.4 mi | 309 ft | Easy |
| Slack Hill Trail | Killington | 2.3 mi | 429 ft | Easy |
| The Lookout via Appalachian Trail | Upper Valley | 4.8 mi | 954 ft | Moderate |
| Windmill Mountain via Holden Trail | Brattleboro | 2.8 mi | 461 ft | Moderate |
| Windmill Mountain via Jamie Latham Trail | Brattleboro | 4.1 mi | 428 ft | Moderate |
| Breakneck Hill via Appalachian Trail | Upper Valley | 3.1 mi | 447 ft | Moderate |
| Cady Hill via Charlie's | Stowe | 2.9 mi | 332 ft | Easy |
| Cady Hill via Snake | Stowe | 1.9 mi | 319 ft | Easy |
| Deer Knoll Loop via Mount Bluff Traili (White) | Manchester | 2.1 mi | 491 ft | Easy |
| Deer Mountain via Hosmer Brook Trail | Groton | 3.9 mi | 880 ft | Moderate |
| Forehead Bypass and Long Trail Loop | Stowe | 1.6 mi | 870 ft | Moderate |
| Gile Mountain via Blue Ribbon Trail | Upper Valley | 5.6 mi | 898 ft | Moderate |
| Griggs Mountain Loop via Appalachian Trail | Upper Valley | 2.5 mi | 540 ft | Moderate |
| Haystack Mountain via North Trail | Northeast Kingdom | 1.7 mi | 867 ft | Moderate |
| Mount Hor via Herbert Hawkes Trail | Northeast Kingdom | 1.6 mi | 658 ft | Easy |
| Thistle Hill via Appalachian Trail | Upper Valley | 3.2 mi | 672 ft | Moderate |
| Austin Hill via Susan Bachner Memorial Trail | Moosalamoo | 2.1 mi | 420 ft | Easy |
| Baker Peak via Griffith Lake Trail | Bromley & Stratton | 9.1 mi | 396 ft | Moderate |
| Bald Top via Cross Rivendell Trail | Groton | 3.1 mi | 933 ft | Moderate |
| Bald Top via Wetlands Trail | Groton | 3.4 mi | 670 ft | Moderate |
| Brigham Hill via Indian Brook Loop Trail | Champlain Valley | 4.4 mi | 493 ft | Moderate |
| Bunker Hill via Appalachian Trail | Upper Valley | 6.1 mi | 1,163 ft | Hard |
| Cushman Hill via Blake Trail | Stowe | 2.1 mi | 393 ft | Easy |
| Dana Hill via Appalachian Trail | Upper Valley | 2.5 mi | 714 ft | Moderate |
| Dana Hill via Evolution | Breadloaf | 2.9 mi | 613 ft | Moderate |
| Dana Hill via Goodnight Irene | Breadloaf | 5.5 mi | 963 ft | Hard |
| Hagar Hill via Appalachian Trail | Glastenbury | 18.4 mi | 1,575 ft | Strenuous |
| Paine Mountain Trail | Groton | 3.3 mi | 879 ft | Moderate |
| Pease Mountain via Upper Loop | Champlain Valley | 2.6 mi | 479 ft | Easy |
| 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 |
| Windmill Mountain via Townline Trail | Brattleboro | 3.8 mi | 909 ft | Moderate |
| Bissell Hill via Shrewsbury Peak Trail | Killington | 4 mi | 577 ft | Moderate |
| Cady Hill Connector | Stowe | 3 mi | 341 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 |
| Mt Ascutney via Summit Trail | Mount Ascutney | 1.3 mi | 309 ft | Easy |
| The Glebe Loop via Fireplace Trail | Upper Valley | 2.1 mi | 559 ft | Easy |
| Appalachian Trail and Heyl Trail Loop | Upper Valley | 2 mi | 366 ft | Easy |
| Chamberlain Hill via Full House | Camel's Hump | 2.5 mi | 622 ft | Moderate |
| Hogback Mountain via Douglas Trail | Brattleboro | 2.4 mi | 340 ft | Easy |
| Hogback Mountain via Hogback Loop Trail | Moosalamoo | 2.1 mi | 343 ft | Easy |
| Hogback Mountain via Raponda Ridge Trail | Brattleboro | 4.6 mi | 545 ft | Moderate |
| Hogback Mountain via Ware Road Connector | Brattleboro | 3.9 mi | 464 ft | Moderate |
| Hogback Mountain via White's Loop | Brattleboro | 2.2 mi | 211 ft | Easy |
| Lookout Rock via Beartown Road | Manchester | 6.5 mi | 1,947 ft | Strenuous |
| Mount Anthony via unmaintained | Bennington | 3.5 mi | 555 ft | Moderate |
| Deer Mountain via Osmore Pond Loop | Groton | 4.5 mi | 534 ft | Moderate |
| Kew Hill via Cyclone Connector | Breadloaf | 3.3 mi | 594 ft | Moderate |
| Kew Hill via Race | Breadloaf | 2.4 mi | 264 ft | Easy |
| Kew Hill via Ridgie | Breadloaf | 2.8 mi | 370 ft | Easy |
| Kew Hill via Swell Hill | Breadloaf | 3.5 mi | 399 ft | Moderate |
| Ridgeline Trail and West Cliff Trail Loop | Brattleboro | 1.3 mi | 172 ft | Easy |
| Russell Hill via Shrewsbury Peak Trail | Killington | 1.2 mi | 195 ft | Easy |
| Griggs Mountain via Appalachian Trail | Upper Valley | 3 mi | 509 ft | Moderate |
| Little Deer Mountain via Big Deer Mountain Trail | Groton | 4.5 mi | 464 ft | Moderate |
| Little Deer Mountain via Osmore Pond Loop | Groton | 2 mi | 273 ft | Easy |
| Red Rock via Henry's Highlands | Camel's Hump | 2.5 mi | 359 ft | Easy |
| Bemis Hill Loop via Hemlock Trail | Brattleboro | 3.2 mi | 484 ft | Moderate |
| Big Deer Mountain Trail | Groton | 3.1 mi | 553 ft | Moderate |
| Devils Hill via Devil's Hill Trail | Groton | 1.7 mi | 343 ft | Easy |
| Marshfield Mountain via Marshfield Ledges approach trail | Groton | 1.6 mi | 440 ft | Easy |
| Moseley Hill via Appalachian Trail | Upper Valley | 2 mi | 366 ft | Easy |
| Neals Hill via Pine Drop | Upper Valley | 3.6 mi | 581 ft | Moderate |
| Shattuck Hill via Brown's Sap Run | Northeast Kingdom | 4.2 mi | 545 ft | Moderate |
| Shattuck Hill via Buzell | Northeast Kingdom | 2.4 mi | 203 ft | Easy |
| Bemis Hill via Athens Access Path | Brattleboro | 1.9 mi | 657 ft | Easy |
| Brigham Hill via Indian Brook Outer Loop | Champlain Valley | 3.6 mi | 405 ft | Moderate |
| Prospect Rock via Appalachian Trail | Bromley & Stratton | 18.3 mi | 699 ft | Strenuous |
| Prospect Rock via Long Trail | Stowe | 1.8 mi | 508 ft | Easy |
| Putney Mountain via Ridgeline Trail | Brattleboro | 1.2 mi | 159 ft | Easy |
| Stratton Mountain via Stratton Ridge Trail | Bromley & Stratton | 1.2 mi | 102 ft | Easy |
| The Glebe via Forest Management Trail | Upper Valley | 2.9 mi | 578 ft | Moderate |
| Neals Hill via Wright Farm Trail | Upper Valley | 1.4 mi | 211 ft | Easy |
| Shaw Hill Loop via Florence | Stowe | 3.3 mi | 356 ft | Easy |
| Austin Hill via Connector Trail | Manchester | 1.6 mi | 232 ft | Easy |
| Barber Hill via Charlotte Village Loop Trail | Champlain Valley | 1.8 mi | 147 ft | Easy |
| Blue Ribbon Trail and Firetower Trail Loop | Upper Valley | 1.2 mi | 279 ft | Easy |
| Cady Hill Loop via Schween Outer | Stowe | 1.5 mi | 190 ft | Easy |
| Chipman Hill via TAM / Sidewinder | Breadloaf | 1.3 mi | 230 ft | Easy |
| Eagle Mountain via Hoyt Lookout Trail | Champlain Valley | 1 mi | 181 ft | Easy |
| Eagle Mountain via Old Orchard Trail | Champlain Valley | 1 mi | 235 ft | Easy |
| Hurricane Hill Loop via Beacon Hill Loop | Upper Valley | 1 mi | 208 ft | Easy |
| Little Pond Mountain via Appalachian Trail | Glastenbury | 9.8 mi | 1,094 ft | Hard |
| Moose Mountain Trail | Northeast Kingdom | 7.9 mi | 1,247 ft | Hard |
| Rice Hill via Loop Trail | Brattleboro | 1.8 mi | 258 ft | Easy |
| Sawyer Mountain Trail | Groton | 2.3 mi | 430 ft | Easy |
| Saxon Hill via Free Fall | Camel's Hump | 1.6 mi | 406 ft | Easy |
| Mount Peg Loop via Constant Flow | Upper Valley | 1.1 mi | 234 ft | Easy |
| Seeley Hill Loop via Loggers' Loop Trail | Stowe | 1.5 mi | 157 ft | Easy |
| Bemis Hill via Hemlock Trail | Brattleboro | 3 mi | 240 ft | Easy |
| Copperas Hill via Copperas Road | Upper Valley | 3.4 mi | 293 ft | Easy |
| Mount Olga via Bishop Trail | Brattleboro | 1.5 mi | 462 ft | Easy |
| Mount Olga via Tower Trail | Brattleboro | 1.1 mi | 253 ft | Easy |
| Oxbow Mountain via Jake | Camel's Hump | 6.6 mi | 1,638 ft | Hard |
| Prospect Rock via Branch Pond Trail | Bromley & Stratton | 14.7 mi | 222 ft | Moderate |
| Spruce Mountain Trail | Groton | 4.2 mi | 1,149 ft | Moderate |
| Chipman Hill Top Trail and TAM / Sidewinder Loop | Breadloaf | 1.1 mi | 198 ft | Easy |
| Lighthouse Hill via Town Highway 64 / Legal Trail 1 | Groton | 1.1 mi | 162 ft | Easy |
| Pine Mountains via Pine Mountain Road | Groton | 3 mi | 231 ft | Easy |
| Spruce Mountain via Spruce - Seyon Trail | Groton | 10.2 mi | 1,737 ft | Strenuous |
| Bald Top via Ackerman Trail | Groton | 1.3 mi | 501 ft | Easy |
| Biscuit Hill via Bourdon Road | Upper Valley | 3.3 mi | 670 ft | Moderate |
| Deer Knoll via Mount Bluff Traili (White) | Manchester | 1.4 mi | 372 ft | Easy |
| East Shaw Hill via Snake | Stowe | 3.1 mi | 229 ft | Easy |
| Millstone Hill via Grand Lookout | Groton | 1.1 mi | 164 ft | Easy |
| Millstone Hill via Roller Coaster | Groton | 1.6 mi | 394 ft | Easy |
| Mount Olga Trail | Brattleboro | 1.4 mi | 525 ft | Easy |
| Owlshead Mountain via Notch Road | Worcester Range | 2.3 mi | 623 ft | Moderate |
| Sable Mountain via Sable Mountain Road | Northeast Kingdom | 9.9 mi | 736 ft | Hard |
| Shaw Hill via Snake | Stowe | 2.7 mi | 290 ft | Easy |
| Shaw Hill via Zog's | Stowe | 3.9 mi | 311 ft | Easy |
| Echo Mountain via Cross Rivendell Trail | Groton | 1.4 mi | 355 ft | Easy |
| Hagar Hill via Little Pond Road | Glastenbury | 2.2 mi | 173 ft | Easy |
| Hurricane Hill via Beacon Hill Loop | Upper Valley | 1.1 mi | 208 ft | Easy |
| Moseley Hill via Heyl Trail | Upper Valley | 1.4 mi | 314 ft | Easy |
| Sykes Hill via Bluff Ridge Trail | Northeast Kingdom | 5.2 mi | 413 ft | Moderate |
| Chipman Hill via The Wall | Breadloaf | 1.4 mi | 348 ft | Easy |
| Emery Mountain via Long Trail | Northern Long Trail | 2.6 mi | 633 ft | Moderate |
| Mount Peg via Dropout | Upper Valley | 1.1 mi | 234 ft | Easy |
| Boyce Hill via Clay Slide Road | Groton | 2 mi | 370 ft | Easy |
| Fassett Hill via National Forest Road 100 | Breadloaf | 2 mi | 235 ft | Easy |
| Fletcher Hill via John Darling Road | Upper Valley | 3 mi | 297 ft | Easy |
| Hurricane Hill via Beard Road | Groton | 1.8 mi | 234 ft | Easy |
| Patch Hill via Piperville Road | Northeast Kingdom | 2.6 mi | 298 ft | Easy |
| Bald Mountain via Sable Mountain Road | Northeast Kingdom | 2 mi | 203 ft | Easy |
| Biscuit Hill via Arhur Morgan Road | Upper Valley | 2.2 mi | 227 ft | Easy |
| Biscuit Hill via Long Hill Road | Upper Valley | 3.1 mi | 113 ft | Easy |
| Liberty Hill via Spike Horn Road | Breadloaf | 4 mi | 429 ft | Moderate |
| Old Buffalo via Scrutton Hill Road | Groton | 2.8 mi | 463 ft | Moderate |
| Prospect Hill Trail | Brattleboro | 1.1 mi | 334 ft | Easy |
| The Hurricane via South Road | Northeast Kingdom | 6.8 mi | 395 ft | Moderate |
| Bill Hill Trail Loop | Upper Valley | 1.7 mi | 270 ft | Easy |
| Lees Hill via Lee's Hill Road | Northeast Kingdom | 3.5 mi | 127 ft | Easy |
| Neals Hill via Reservoir Road | Upper Valley | 2.7 mi | 226 ft | Easy |
| Castle Hill via Cobb Hill Road | Moosalamoo | 1.9 mi | 387 ft | Easy |
| Pond Circuit Trail and Ridgeline Trail and Carriage Barn Link | Stowe | 2.9 mi | 393 ft | Easy |
| Bill Hill Trail | Upper Valley | 1 mi | 219 ft | Easy |
| Delectable Mountain via Smith Hill Road | Upper Valley | 1.1 mi | 373 ft | Easy |
| Flag Hill via Cross Rivendell Trail | Groton | 1.5 mi | 451 ft | Easy |
| The Saddle via Ridgeline Trail | Stowe | 2.6 mi | 362 ft | Easy |
| Indian Lookout Loop | Camel's Hump | 1.1 mi | 200 ft | Easy |
| Alder Hill via Town Highway 17 | Breadloaf | 1.8 mi | 125 ft | Easy |
| Buzzell Hill via Brown Road | Northeast Kingdom | 1.3 mi | 105 ft | Easy |
| Coombs Hill via Town Highway 13 | Northern Long Trail | 1.2 mi | 222 ft | Easy |
| Toot Hill via Grimes Road | Northeast Kingdom | 1.3 mi | 117 ft | Easy |
| Ross Hill via Ross Hill Road | Stowe | 1.3 mi | 120 ft | Easy |
| May Hill via Brushwood Road | Groton | 3.3 mi | 374 ft | Easy |
| May Hill via Cross Mountain Road North | Groton | 1.9 mi | 401 ft | Easy |
| May Hill via Mill Pond Road | Groton | 2.1 mi | 218 ft | Easy |
RidgeSync