Home › Features › Hilly Trails & Hill Workouts › Massachusetts
Hilly Trails & Hill Workouts in Massachusetts
Massachusetts has 187 trails with hills and elevation in this directory, across 117 cities and towns — Worcester, Medfield, Andover, Littleton and 113 more. Climbing and vert — hill repeats, and the strength flat running never builds.
Every one in Massachusetts
Use the filters to narrow these by surface, loop, distance, shade, lighting, restrooms, water and parking.
Middlesex Fells Reservation
4.7 ★★★★★ 5,506 reviews
2,575-acre natural haven including hiking trails around a pond, plus areas for dog-walking & biking.
Wachusett Mountain State Reservation
4.7 ★★★★★ 4,269 reviews
Protected area including roadways to the summit, 17 miles of hiking & biking trails & ski slopes.
Green Hill Park
4.6 ★★★★★ 2,462 reviews
480-acre park with sports, playgrounds, trails, a petting zoo, a golf course & picnic facilities.
Breakheart Reservation
4.7 ★★★★★ 2,308 reviews
This forest with hiking trails, lakes & a river offers activities such as fishing & swimming.
Fort Phoenix State Reservation
4.6 ★★★★★ 1,689 reviews
Scenic bay views, hiking & a half-mile swimming beach draw locals & visitors to this historic park.
World's End
4.7 ★★★★★ 1,607 reviews
This tranquil coastal park offers scenic views of the Boston skyline, plus 4.5 miles of trails.
Mount Tom State Reservation
4.8 ★★★★★ 1,458 reviews
State park with scenic views boasts premier spot for hawk-watching, plus skiing, fishing & skating.
Larz Anderson Park
4.7 ★★★★★ 1,371 reviews
This landscaped park offers pathways, ponds, gardens, a skating rink & an auto museum.
Danehy Park
4.7 ★★★★★ 1,266 reviews
50-acre green space with activities such as softball & soccer, plus paths for jogging & a dog park.
Freedom Trail
4.8 ★★★★★ 1,233 reviews
Historical landmark and hiking area with a cemetery offering free admission.
Horn Pond Recreation Area
4.7 ★★★★★ 1,100 reviews
Scenic area next to a large pond offering outdoor activities such as hiking & biking.
Millennium Park
4.7 ★★★★★ 1,036 reviews
Natural retreat with 6 miles of accessible trails, playing fields, a canoe launch & scenic views.
Moore State Park
4.8 ★★★★★ 952 reviews
Tranquil, densely-forested area with short hiking trails, picturesque old mills & a charming pond.
Skinner State Park
4.8 ★★★★★ 933 reviews
Home to the Summit House, a historic hotel, this park offers hiking trails with scenic river views.
Mount Sugarloaf State Reservation
4.8 ★★★★★ 871 reviews
Hiking trails & an auto road ascend the summit, where a picnic pavilion affords mountaintop views.
Fellsmere Park
4.6 ★★★★★ 760 reviews
Comprising grassy & wooded areas, this serene park features a walking path & a pond with a fountain.
Mount Holyoke Range State Park
4.7 ★★★★★ 726 reviews
3,000-acre lava rock range with thickets of forest, 30 miles of hiking trails & winter sports.
Houghton's Pond Recreation Area
4.6 ★★★★★ 643 reviews
Popular destination for picnics and grilling, with a playground and beach.
Prospect Hill Park
4.7 ★★★★★ 621 reviews
Uphill hiking trails (some paved) and roadways lead to scenic overlooks at this hilly park with Boston views, plus a playground, picnic tables and grills.
Leominster State Forest
4.6 ★★★★★ 621 reviews
Destination for activities such as hiking, fishing, mountain climbing & cross-country skiing.
Barrett Park
4.6 ★★★★★ 603 reviews
Large locale featuring a pond with hiking trails, a fountain and a playground.
Callahan State Park
4.5 ★★★★★ 607 reviews
Trails for mountain biking, hiking, cross-country skiing, horseback riding, plus 100 acres of field.
Nonotuck Park
4.6 ★★★★★ 573 reviews
Outdoor green space featuring playgrounds, baseball fields and tennis courts, plus a pool.
The Knob
4.8 ★★★★★ 514 reviews
Nature area on a rocky hill overlooking Buzzards Bay offering hiking paths, swimming & sunset views.
Westville Recreation Area
4.7 ★★★★★ 517 reviews
Year-round spot for outdoor activities, featuring hiking trails, picnic areas with grills & a lake.
Charles W. Ward Reservation
4.8 ★★★★★ 492 reviews
Hiking area offering dog-friendly trails, some with views of Boston, plus a fire tower.
Fort Revere Park
4.5 ★★★★★ 515 reviews
Hilltop historical area with old military bunkers, offering panoramic views of Boston Harbor.
Wahconah Falls State Park
4.7 ★★★★★ 489 reviews
48-acre wooded state park with waterfalls, picnic areas & hiking trails, plus fishing & restrooms.
Blue Hills - Skyline Trail
4.7 ★★★★★ 476 reviews
Young, forested reserve for hiking as well as scenic views of Boston’s skyline.
Mass Audubon's Pleasant Valley Wildlife Sanctuary
4.8 ★★★★★ 464 reviews
Nature walks & rugged hikes in a landscape of forests, meadows & marshes known for resident beavers.
Doane's Falls
4.8 ★★★★★ 433 reviews
Short, well-maintained hiking trail showcasing 3 waterfalls along the route.
Noanet Woodlands
4.7 ★★★★★ 408 reviews
Woodsy preserve featuring 17 miles of hiking trails, bird-watching & city views from Noanet Peak.
Mass Audubon's Stony Brook Wildlife Sanctuary
4.8 ★★★★★ 386 reviews
Family-friendly site featuring a pond, wetlands, trails, boardwalks and wildlife.
Watatic Mountain State Wildlife Area
4.7 ★★★★★ 369 reviews
Scenic views (including Boston) & diverse wildlife draw crowds to this rugged hiking destination.
Groff Park
4.7 ★★★★★ 363 reviews
14-acre green space with ball fields, picnic areas & BBQs, plus a playground, trail & shallow river.
Rocky Woods
4.8 ★★★★★ 355 reviews
Known for its 6+ miles of hiking trails, this natural area features woods, wetlands & ponds.
Cold Spring Park
4.7 ★★★★★ 361 reviews
This green space with wooded areas & fields offers a dog park, exercise path & athletic facilities.
Chestnut Hill Reservation
4.8 ★★★★★ 348 reviews
Reservoir surrounded by trees and trails, popular for joggers, cyclists and dog-walkers.
Menotomy Rocks Park
4.7 ★★★★★ 350 reviews
Spread among the grounds are wooded trails, ball fields, a 3-acre fishing pond & a playground.
Wachusett Dam and Wachusett Reservoir
4.8 ★★★★★ 332 reviews
Park on 2.2 square miles around a reservoir, offering picnicking, hiking, winter sports & fishing.
Cascading Waters
4.5 ★★★★★ 349 reviews
Waterfall, cascades, and trails and park amid woodland views.
Blackstone River and Canal Heritage State Park
4.7 ★★★★★ 317 reviews
A 1,000-acre park featuring canoeing, walking and hiking paths, and nature exhibits.
Great Island Trail
4.8 ★★★★★ 305 reviews
Well-known coastal area featuring dunes, hiking trails, seals, marshes, wildlife and a cliff.
Upton State Forest
4.6 ★★★★★ 314 reviews
Woodland park with Great Depression heritage including trails for hiking, skiing, riding & bikes.
Skyline Park
4.6 ★★★★★ 307 reviews
Park with turf soccer fields, walking paths and playgrounds, plus picnic areas.
Rogers Fort Hill Park
4.6 ★★★★★ 303 reviews
Serene park featuring grassy areas and a fountain, plus trails, plus spaces for kids to play.
Rock Meadow Conservation Area
4.8 ★★★★★ 290 reviews
Public conservation land of meadow, wetlands, streams & woods, plus updated Belmont Victory Gardens.
Trustees of Reservations
4.9 ★★★★★ 280 reviews
Nature preserve featuring carriage roads and walking trails, some with ocean views.
Bell Rock Memorial Park
4.5 ★★★★★ 287 reviews
Public park featuring benches, a small grassy area, and memorials to fallen soldiers.
Cascade Trail - Trailhead
4.6 ★★★★★ 279 reviews
Family-friendly hiking trail through the woods to a waterfall.
Warren H Manning State Forest
4.6 ★★★★★ 269 reviews
Small, forested natural area with walking paths, a water playground & picnic tables.
Pratt Farm
4.6 ★★★★★ 254 reviews
Leisurely space for walking trails (some steep, others easy) through hilly woodland.
Breakheart Reservation Wakefield Entrance
4.7 ★★★★★ 245 reviews
Peaceful park with a lake and a beach for swimming and walking, plus picnic areas and playgrounds.
Russell Mill Pond and Town Forest
4.7 ★★★★★ 237 reviews
Trails for hiking and mountain biking around a pond with fishing.
Whipple Hill
4.5 ★★★★★ 240 reviews
This 120-acre conservation area offers 4 miles of trails, a pond & lots of plant & animal life.
Kennedy Park
4.6 ★★★★★ 233 reviews
Wooded area featuring hiking, biking and picnic areas amid scenic trails.
Wrentham State Forest
4.4 ★★★★☆ 239 reviews
Trail-filled nature preserve offering hiking and mountain-bike trails and a dirt-bike area.
Frothingham Park
4.6 ★★★★★ 227 reviews
Neighborhood park featuring a playground, basketball courts and baseball fields.
Wilson Mountain Reservation
4.5 ★★★★★ 229 reviews
Family-friendly and dog-friendly tract featuring two marked paths through woods and rocky terrain and a hilltop vista.
Great Esker Park
4.6 ★★★★★ 217 reviews
Glacial gravel ridge with canoe rentals, trails, playgrounds, sports fields & river views.
Den Rock Park
4.4 ★★★★☆ 224 reviews
120-acre nature preserve with wooded walking trails & a granite face for rock climbing.
Cascades Park
4.6 ★★★★★ 214 reviews
Park featuring trails of varying difficulty, plus cascades and views of nature.
Adams Farm
4.6 ★★★★★ 202 reviews
Winding trails, a community garden and a barn are just some of the attractions at this family-friendly park.
Oak Hill Conservation Land
4.6 ★★★★★ 200 reviews
Nature preserve featuring hiking trails and scenic views.
Leadmine Mountain Trail (Main Entrance)
4.7 ★★★★★ 191 reviews
Tranquil hiking area with gravel tracks around a scenic pond and through woodland.
Reservoir Park
4.6 ★★★★★ 193 reviews
City views plus a track for runners, a reservoir and hills for sledding.
Mount Toby State Forest
4.7 ★★★★★ 187 reviews
Nature preserve featuring hiking trails, a waterfall, and a fire tower, among other attractions.
Parkhill Park
4.1 ★★★★☆ 214 reviews
Pipes and ramps for rollerblading, skateboarding and biking as well as a playground area.
Billerica State Forest
4.5 ★★★★★ 194 reviews
Urban green space providing rustic, multi-use trails & wooded areas for walking & wildlife viewing.
Hammond Pond Reservation
4.7 ★★★★★ 178 reviews
This scenic area with a forest & large pond offers fishing, rock climbing & hiking on wooded trails.
Gallows Hill Park
4.1 ★★★★☆ 195 reviews
Small, scenic park for skateboarding, soccer and baseball games, plus a playground.
West Hill Dam
4.8 ★★★★★ 161 reviews
Clean, well-maintained park featuring trails for walkers and mountain bikers, plus a lake beach.
Mass Central Rail Trail (West Boylston)
4.7 ★★★★★ 164 reviews
Hiking, biking, and dog walking are allowed on this quiet trail with picnic tables.
Highland Park
4.6 ★★★★★ 158 reviews
Family-friendly park featuring trails for hiking, walking and running.
Ali's Park of Eastondale
4.7 ★★★★★ 153 reviews
Popular playground featuring swings, slides and more.
Hoosac Range Reserve
4.8 ★★★★★ 138 reviews
Hiking area with well-marked trails leading to the summit of Spencer Hill for far-reaching views.
Prospect Park
4.4 ★★★★☆ 148 reviews
Woodsy park featuring leafy trails and a pagoda, as well as ruins from a former estate.
Weir Hill
4.8 ★★★★★ 134 reviews
Park featuring a lake and a hilltop with views, plus trails for hiking and dog walking.
Peppercorn Hill Conservation Area
4.7 ★★★★★ 133 reviews
Forested 283-acre conservation area with vistas, streams & wetlands, plus trails for hiking.
Abram's Rock
4.6 ★★★★★ 134 reviews
Destination featuring historical landmarks, hiking trails, and mountain biking opportunities.
Noon Hill Reservation
4.7 ★★★★★ 131 reviews
Local 20-minute or hour-long hike with steep parts, along with a pond, forest and views of Gillette Stadium.
Veteran's Freedom Park
4.6 ★★★★★ 133 reviews
Relaxed park featuring a lake, trails through the woods, rolling hills, a tennis court and picnic tables.
Gammino Pond Preserve
4.7 ★★★★★ 124 reviews
Hikers and dog walkers come to this preserved spot for scenic trails with picnic spots as well.
J.C. Phillips Nature Preserve
4.7 ★★★★★ 123 reviews
Nature preserve featuring trails, lake access, and ruins, plus dog-friendly walking.
Assabet River Rail Trail - East Hudson Trailhead
4.6 ★★★★★ 125 reviews
Paved biking and walking trail that extends for about 2 hours.
Laughing Brook Wildlife Sanctuary
4.5 ★★★★★ 125 reviews
Park with marked trails through wooded terrain, plus picnic tables and a gazebo.
Great Meadows National Wildlife Refuge
4.5 ★★★★★ 123 reviews
Wetland habitat offering nature trails for bird-watching & other wildlife viewing.
Batchelder Park
4.6 ★★★★★ 118 reviews
Park offering trails for walking, running, and hiking, with a scenic overlook.
Mass Audubon's High Ledges Wildlife Sanctuary
4.7 ★★★★★ 106 reviews
Outdoor, rugged area with trails, cascades, ponds, and ledges.
Goldsmith Woodlands
4.6 ★★★★★ 107 reviews
Nature preserve offering a variety of hiking trails and multiple viewpoints overlooking Foster's Pond.
Deer Jump Reservation - A.V.I.S
4.6 ★★★★★ 106 reviews
Park offering a riverside path that's suitable for hiking, biking, and walking.
Rice Preserve / Sunrise Peak Trailwalk
4.7 ★★★★★ 103 reviews
Overlook featuring hiking trails, plus views of Vermont and the Holyoke Range.
Lowell Holly Reservation
4.7 ★★★★★ 100 reviews
Park featuring a peaceful beach, clear pond water, well-maintained paths and woodland views.
Woodsom Farm Park
4.7 ★★★★★ 100 reviews
Park offering hiking, jogging, and sledding, as well as space for dog walking.
Bay Farm Trails
4.7 ★★★★★ 95 reviews
Park and farm featuring trails with ocean vistas along with a beach.
Seven Hills Park
4.2 ★★★★☆ 102 reviews
Park in Davis Square with a bike path, open space, and music, good for kids.
Beverly Commons Conservation Area
4.7 ★★★★★ 87 reviews
Recreation area with trails for hiking, mountain biking, and off-leash dogs.
The Cascade
4.7 ★★★★★ 87 reviews
Park featuring short, easy trails leading to a picturesque waterfall for photo ops.
Prospect Hill (Lookout - View of Boston)
4.8 ★★★★★ 85 reviews
Park with picnic tables and walking trails, offering Boston views from the hilltop.
Mass Audubon Burncoat Pond Wildlife Sanctuary
4.4 ★★★★☆ 91 reviews
Kid-friendly park featuring meadows and well-maintained trails for walking and hiking.
Tippling Rock
4.6 ★★★★★ 87 reviews
Wooded trail leading to a peak with views of Boston and the surrounding area.
Whitney and Thayer Woods
4.7 ★★★★★ 83 reviews
Serene woodland park with 10 miles of trails, meadows & unique glacier boulders, plus city vistas.
Oak Hill Reservation Lookout Rock Trailhead
4.7 ★★★★★ 83 reviews
Hiking area with trails offering views, waterfalls, springs, and wetlands.
Hamlen Woods
4.8 ★★★★★ 81 reviews
Lakeside woods offering easy-to-moderate hiking routes, as well as a run and ski trail.
1st Lt. Arthur E. Farnham, Jr., and SSgt. Thomas M. Connolly, Jr. Memorial Park
4.4 ★★★★☆ 88 reviews
Park, formerly an airport, offering grassy areas and a long trail.
Rice City Pond
4.6 ★★★★★ 84 reviews
Easy, clean and peaceful terrain for walking and hiking, set among forests, rivers and vistas.
Waitts Mount Park
4.8 ★★★★★ 78 reviews
Relaxed refuge featuring basketball courts and playgrounds for kids, plus a stone climber and a hiking trail.
Jamison Sullivan North Hill Marsh Wildlife Sanctuary
4.5 ★★★★★ 83 reviews
Wildlife refuge with trails for hiking and walking around a cranberry bog, ponds, and stone walls.
Edmands Park
4.6 ★★★★★ 79 reviews
Leafy 33-acre park gifted to the city in 1913, offering natural unpaved trails & a wooded area.
Salem Woods Highland Park
4.4 ★★★★☆ 82 reviews
Destination for tranquil nature hikes through a large woodland park with marked trails.
Crane Swamp
4.2 ★★★★☆ 81 reviews
This vast natural area surrounding a 400-acre swamp features trails, forests & diverse wildlife.
Bearsden Forest Conservation Area
4.5 ★★★★★ 75 reviews
Historic wilderness area contains trails, camping sites, bridges, old quarries, ponds & brooks.
Danforth Falls Trailhead
4.4 ★★★★☆ 75 reviews
Family-friendly, maintained nature trails featuring picturesque waterfalls and a stream, plus wildflowers.
Mineral Hills Conservation Area
4.7 ★★★★★ 67 reviews
Expansive hillside preserve featuring striking forested landscape, seasonal creeks & hiking trails.
Noon Hill Reservation Trail Head
4.7 ★★★★★ 64 reviews
Nature preserve featuring trails with scenic views, a pond, and a running creek.
Mt. Pollux Conservation Area
4.6 ★★★★★ 65 reviews
Nature preserve offering kid-friendly hikes and picnicking.
Maple Swamp
4.8 ★★★★★ 58 reviews
Park featuring a wide variety of hiking and biking trails, from easy to challenging.
Hill's Hill
4.5 ★★★★★ 61 reviews
Recreational park with a baseball field, soccer field, playground, picnic tables, and bike paths.
Red Maple Swamp Trail
4.8 ★★★★★ 57 reviews
Family-friendly wetland area featuring scenic trails, a boardwalk and a gazebo.
Old Town Hill Reservation
4.7 ★★★★★ 56 reviews
Nature preserve featuring paths leading to a hilltop with coastal views, plus picnic spots.
Mass Audubon's Flat Rock Wildlife Sanctuary
4.4 ★★★★☆ 58 reviews
Wooded area with hiking trails providing habitat for various species.
Edmund Hill Woods
4.4 ★★★★☆ 58 reviews
Hiking area suitable for children with frequent mention of dogs and bug spray.
God's Acre
4.2 ★★★★☆ 59 reviews
Nature preserve with forest trails and kid-friendly hiking options.
College Rock Park
4.7 ★★★★★ 52 reviews
Top-roping destination featuring a 40-ft high wall and a network of trails.
Mass Audubon's Rocky Hill Wildlife Sanctuary
4.2 ★★★★☆ 58 reviews
Trails wind past caves, rock formations and boulders, as well as swamps.
Cedariver
4.7 ★★★★★ 42 reviews
Kid-friendly hiking area offering a short trail that runs along a river and through woods.
Red Rocks Conservation Area
4.7 ★★★★★ 41 reviews
Forested locale with walking trails that's popular for rock climbing and hiking, plus ocean views.
Mass Audubon's Pierpont Meadow Wildlife Sanctuary
4.5 ★★★★★ 42 reviews
Wildlife refuge offering a kid-friendly hike, trails, and wildflowers.
Wilmington Town Forest
4.2 ★★★★☆ 43 reviews
Mount Warner
4.5 ★★★★★ 36 reviews
Hiking area with mostly wide, easy trails that's good for kids.
Southwick Pond
4.8 ★★★★★ 33 reviews
McCarthy Park and Fields
4.5 ★★★★★ 28 reviews
Fish Park
4.3 ★★★★☆ 22 reviews
Sen Ki - Hale Reservation
4.4 ★★★★☆ 18 reviews
West Concord Park
4.2 ★★★★☆ 5 reviews
Great Blue Hill Summit Road
4 ★★★★☆ 3 reviews
No trails match those filters.
By city
Every running trail in the town, not just the ones with hills and elevation.
- Worcester
- Medfield
- Andover
- Littleton
- Malden
- Acton
- Amherst
- Concord
- Duxbury
- Hingham
- Newton
- North Adams
- Northborough
- Plymouth
- Sturbridge
- Uxbridge
- Westford
- Amesbury
- Arlington
- Athol
- Beverly
- Boston
- Canton
- Dudley
- Fitchburg
- Gloucester
- Groton
- Hadley
- Hudson
- Lawrence
- Lenox
- Mashpee
- Milton
- North Andover
- Pittsfield
- Quincy
- Salem
- Sharon
- Stoneham
- Sudbury
- Upton
- Wakefield
- Waltham
- Weymouth
- Williamstown
- Adams
- Ashburnham
- Ayer
- Belmont
- Billerica
- Brewster
- Brighton
- Brookline
- Buzzards Bay
- Cambridge
- Chelmsford
- Chestnut Hill
- Clinton
- Cohasset
- Dalton
- Dedham
- Dover
- Dracut
- East Sandwich
- Eastham
- Easthampton
- Fairhaven
- Falmouth
- Framingham
- Greenfield
- Hampden
- Haverhill
- Holyoke
- Hopkinton
- Hull
- Kingston
- Leicester
- Leominster
- Leverett
- Lexington
- Lowell
- Marlborough
- Middleborough
- Millbury
- Millis
- Needham
- Newbury
- Norfolk
- North Billerica
- North Easton
- Northampton
- Orange
- Paxton
- Princeton
- Royalston
- Sandwich
- Saugus
- Seekonk
- Shelburne Falls
- Shrewsbury
- Somerville
- South Deerfield
- South Easton
- Spencer
- Stow
- Swansea
- Walpole
- Wayland
- Wellfleet
- West Boylston
- Westborough
- Westminster
- Westwood
- Wilbraham
- Wilmington
- Woburn
- Wrentham
See hilly trails & hill workouts across the whole country, or every running trail in Massachusetts. You can also browse the other features or start from surface.