| Mount Mansfield via Hell Brook Trail | Stowe | 2.6 mi | 2,446 ft | Hard |
| Jay Peak via Long Trail | Northern Long Trail | 3 mi | 1,621 ft | Moderate |
| Mount Anthony via Summit Trail | Bennington | 2.3 mi | 1,238 ft | Moderate |
| Big Rock Hill via Summit Loop Trail | Northeast Kingdom | 2.3 mi | 612 ft | Moderate |
| Bald Mountain via Aitken State Forest Trail | Killington | 2.7 mi | 708 ft | Moderate |
| Neals Hill Loop via Wright Farm Trail | Upper Valley | 2.1 mi | 397 ft | Easy |
| 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 |
| 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 |
| Beane Mountain via Long Trail | Camel's Hump | 2.7 mi | 739 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 |
| Owls Head via Gilberts Lookout (Blue) | Manchester | 2.8 mi | 1,170 ft | Moderate |
| Dana Hill via Enchanted Forest Trail | Breadloaf | 3 mi | 278 ft | Easy |
| Deer Knoll via Trout Lily Trail (White Purple) | Manchester | 2.4 mi | 558 ft | Moderate |
| Slab Trail and Summit Trail Loop | Mount Ascutney | 1.4 mi | 309 ft | Easy |
| Slack Hill Trail | Killington | 2.3 mi | 429 ft | Easy |
| Windmill Mountain via Holden Trail | Brattleboro | 2.8 mi | 461 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 |
| Forehead Bypass and Long Trail Loop | Stowe | 1.6 mi | 870 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 |
| Austin Hill via Susan Bachner Memorial Trail | Moosalamoo | 2.1 mi | 420 ft | Easy |
| 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 |
| 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 |
| 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 White's Loop | Brattleboro | 2.2 mi | 211 ft | Easy |
| Kew Hill via Race | Breadloaf | 2.4 mi | 264 ft | Easy |
| Kew Hill via Ridgie | Breadloaf | 2.8 mi | 370 ft | Easy |
| 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 Osmore Pond Loop | Groton | 2 mi | 273 ft | Easy |
| Red Rock via Henry's Highlands | Camel's Hump | 2.5 mi | 359 ft | Easy |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| Mount Olga via Bishop Trail | Brattleboro | 1.5 mi | 462 ft | Easy |
| Mount Olga via Tower Trail | Brattleboro | 1.1 mi | 253 ft | Easy |
| Chipman Hill Top Trail and TAM / Sidewinder Loop | Breadloaf | 1.1 mi | 198 ft | Easy |
| Crescent Lake Trail | Upper Valley | 2 mi | 123 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 |
| Bald Top via Ackerman Trail | Groton | 1.3 mi | 501 ft | Easy |
| Deer Knoll via Mount Bluff Traili (White) | Manchester | 1.4 mi | 372 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 |
| Shaw Hill via Snake | Stowe | 2.7 mi | 290 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 |
| Chipman Hill via The Wall | Breadloaf | 1.4 mi | 348 ft | Easy |
| Crescent Lake Trail Loop | Upper Valley | 1.7 mi | 318 ft | Easy |
| Emery Mountain via Long Trail | Northern Long Trail | 2.6 mi | 633 ft | Moderate |
| Milton Pond via Town Forest Access Trail | Stowe | 2.4 mi | 176 ft | Easy |
| Mount Peg via Dropout | Upper Valley | 1.1 mi | 234 ft | Easy |
| Boyce Hill via Clay Slide Road | Groton | 2 mi | 370 ft | Easy |
| Cort's Jester Loop | Mount Ascutney | 2.4 mi | 406 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 |
| Pond View Loop via Pond Circuit Trail | Stowe | 2.8 mi | 314 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 |
| Cold River Vista via Aitken State Forest Trail | Killington | 2.2 mi | 722 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 |
| Silent Cliff via Long Trail | Breadloaf | 1.5 mi | 396 ft | Easy |
| Bill Hill Trail Loop | Upper Valley | 1.7 mi | 270 ft | Easy |
| Bolton Firetower Loop via Cobrass Run | Worcester Range | 2.6 mi | 1,032 ft | Moderate |
| Neals Hill via Reservoir Road | Upper Valley | 2.7 mi | 226 ft | Easy |
| Pond Circuit Trail and Ridgeline Trail | Stowe | 2 mi | 405 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 |
| Beacon Hill Vista via Beacon Hill Loop | Upper Valley | 2.3 mi | 570 ft | Moderate |
| Chipman Hill viewpoint via TAM / Sidewinder | Breadloaf | 2.7 mi | 427 ft | Easy |
| Green Chair II via Cady Hill Climb | Stowe | 2.1 mi | 207 ft | Easy |
| Green Chair Overlook via Florence | Stowe | 1.9 mi | 230 ft | Easy |
| Libby's Look via Libby's Look Loop | Camel's Hump | 1.9 mi | 331 ft | Easy |
| Mansfield View via Pond Circuit Trail | Stowe | 1.9 mi | 304 ft | Easy |
| green trail and Lewis Deane Original Trail Loop | Manchester | 1.8 mi | 554 ft | Easy |
| Indian Brook Outer Loop | Champlain Valley | 2 mi | 333 ft | Easy |
| Pond Circuit Trail and Ridgeline Trail and Carriage Barn Link (2.4 mi) | Stowe | 2.4 mi | 288 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 |
| Discovery Trail | Manchester | 2.6 mi | 647 ft | Moderate |
| Flag Hill via Cross Rivendell Trail | Groton | 1.5 mi | 451 ft | Easy |
| Red Rock Pond via Pond Summit Trail | Moosalamoo | 2.7 mi | 815 ft | Moderate |
| The Saddle via Ridgeline Trail | Stowe | 2.6 mi | 362 ft | Easy |
| Tinmouth Ridge Trail | Killington | 2.1 mi | 811 ft | Moderate |
| Ursa Way | Bennington | 2.4 mi | 785 ft | Moderate |
| Forehead Bypass and Long Trail Loop and Wampahoofus Trail | Stowe | 2 mi | 1,056 ft | Moderate |
| 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 |
| Kents ledge trail | Upper Valley | 2.2 mi | 756 ft | Moderate |
| Toot Hill via Grimes Road | Northeast Kingdom | 1.3 mi | 117 ft | Easy |
| Charlie's and Florence Loop | Stowe | 1.4 mi | 193 ft | Easy |
| Ross Hill via Ross Hill Road | Stowe | 1.3 mi | 120 ft | Easy |
| Summit Trail and Zaphod's Run Loop | Bennington | 1.7 mi | 692 ft | Easy |
| Chipman Hill viewpoint via Northern Loop | Breadloaf | 1.9 mi | 297 ft | Easy |
| Green Chair Overlook via Cady Hill Connector | Stowe | 2.1 mi | 113 ft | Easy |
| Overlook | Killington | 2.9 mi | 406 ft | Easy |
| Robert's Way | Champlain Valley | 2.5 mi | 219 ft | Easy |
| Sucker Brook Hollow Trail | Champlain Valley | 2 mi | 438 ft | Easy |
| Taft Lodge via Hell Brook Trail | Stowe | 2.5 mi | 1,692 ft | Moderate |
| Warren Path | Breadloaf | 2.5 mi | 450 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 |
| Amity Pond Trail | Upper Valley | 2.7 mi | 630 ft | Moderate |
| Devil's Den via Nancy's Trace | Groton | 2 mi | 371 ft | Easy |
| Devil's Den via Rube's Trail | Groton | 2.2 mi | 592 ft | Moderate |
| Falls of Lana via Lower Cliff Trail | Moosalamoo | 1.3 mi | 254 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 |
| Chipman Hill viewpoint Loop via Chipman Hill Top Trail | Breadloaf | 1.3 mi | 226 ft | Easy |
| Eastern Meadow Trail Loop | Moosalamoo | 1.5 mi | 232 ft | Easy |
| Ice Bed Trail Loop | Killington | 1.7 mi | 355 ft | Easy |
| Zaphod's Run | Bennington | 1.4 mi | 620 ft | Easy |
| Beacon Hill Loop and Tower Trail | Upper Valley | 1.5 mi | 322 ft | Easy |
| Ledges overlook trail Loop | Brattleboro | 1.4 mi | 641 ft | Easy |
| Farm Trail | Manchester | 2 mi | 505 ft | Easy |
| Faulkner Trail | Upper Valley | 2.8 mi | 464 ft | Moderate |
| Forehead Bypass | Stowe | 2.4 mi | 212 ft | Easy |
| Grime's Grind | Bennington | 2.8 mi | 576 ft | Moderate |
| Hunker Down | Manchester | 2.1 mi | 560 ft | Easy |
| Ice Bed Trail | Killington | 2 mi | 378 ft | Easy |
| Shale Shifter | Manchester | 2.4 mi | 415 ft | Easy |
| Pleasant Valley Reservoir via French Road | Brattleboro | 1.9 mi | 120 ft | Easy |
| Beacon Hill Vista via WB Brown Trail | Upper Valley | 1.1 mi | 153 ft | Easy |
| Clarendon Shelter via Appalachian Trail | Killington | 2.2 mi | 587 ft | Moderate |
| Green Chair II via Bridgey | Stowe | 1.7 mi | 223 ft | Easy |
| Green Chair Overlook via Bear's | Stowe | 1.1 mi | 228 ft | Easy |
| Healdville Trail | Killington | 3 mi | 1,895 ft | Hard |
| Lewis Deane Original Trail | Manchester | 1.6 mi | 509 ft | Easy |
| Norwich Reservoir via Grow Place Road | Groton | 2.5 mi | 517 ft | Moderate |
| Peak A View via Sterling Run | Stowe | 1.6 mi | 274 ft | Easy |
| Raven Ridge Trail | Champlain Valley | 1.3 mi | 282 ft | Easy |
| Vista Trail (Blue) | Killington | 1 mi | 272 ft | Easy |
| Laird's Loop | Killington | 1.6 mi | 446 ft | Easy |
| Meadow Trail and South Meadow Trail Loop | Moosalamoo | 1.2 mi | 222 ft | Easy |
| Ledges overlook trail | Brattleboro | 1.6 mi | 630 ft | Easy |
| Roundtop Shelter via Long Trail | Stowe | 2.7 mi | 728 ft | Moderate |
| Amity Pond Shelter Loop via Amity Pond Trail | Upper Valley | 1.5 mi | 303 ft | Easy |
| Bishop Trail and Rim Run Loop | Brattleboro | 1.9 mi | 469 ft | Easy |
| South Meadow Trail | Moosalamoo | 1 mi | 222 ft | Easy |
| Amity Pond Trail (2.1 mi) | Upper Valley | 2.1 mi | 584 ft | Easy |
| Hogback Loop Trail | Moosalamoo | 2.2 mi | 250 ft | Easy |
| Pine via House Rock Trail | Champlain Valley | 1.4 mi | 444 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 |
| Tom G's | Stowe | 1.9 mi | 353 ft | Easy |
| Story Spring Shelter Loop via Appalachian Trail | Bromley & Stratton | 1.5 mi | 265 ft | Easy |
| Darling Road Trail | Groton | 1.6 mi | 489 ft | Easy |
| Eagle's Trail | Camel's Hump | 1.7 mi | 321 ft | Easy |
| Revolution | Worcester Range | 1 mi | 331 ft | Easy |
| CCC Trail | Killington | 1.4 mi | 741 ft | Easy |
| Ledges overlook trail (1.4 mi) | Brattleboro | 1.4 mi | 630 ft | Easy |
| Cloudland Shelter via Appalachian Trail | Upper Valley | 1.4 mi | 264 ft | Easy |
| Governor Clement Shelter via Appalachian Trail | Killington | 1.4 mi | 142 ft | Easy |
| Story Spring Shelter via Appalachian Trail | Bromley & Stratton | 1.5 mi | 216 ft | Easy |
| Burnham Down | Northeast Kingdom | 1.5 mi | 321 ft | Easy |
| Davy Trail | Worcester Range | 1.8 mi | 542 ft | Easy |
| Heyl Trail | Upper Valley | 1.2 mi | 257 ft | Easy |
| Kent Brook Trail | Killington | 1 mi | 206 ft | Easy |
| Mount Olga Trail (1.5 mi) | Brattleboro | 1.5 mi | 389 ft | Easy |
| Notch Trail | Groton | 1.1 mi | 430 ft | Easy |
| Pollard Hill | Northeast Kingdom | 1.3 mi | 286 ft | Easy |
| Rich Trail | Mount Ascutney | 1.4 mi | 393 ft | Easy |