If you’re an outdoor enthusiast and are planning to be in the Portland, Maine area, be sure to set aside time for day hiking—and, despite the relatively urban location, you won’t have to drive for too long to reach most of these trailheads.
One of the many great things about Vacationland is that you’re never far from gorgeous views, whether they include panoramas of mountaintops, undulating rocky coastlines, forests, and meadowlands…or all of the above.
And, accordingly, the variety of hikes on offer in the Portland area range from easy, short, and flat to steep, rugged, and long…and everything in between.
Here are ten of my picks for the most popular hikes in the Portland and Southern Maine area; you’re sure to find one that suits your mood and abilities (oh, and I’ve also included a recommendation for after-hike pub visits for each spot, because that’s how I roll).
As with any hike in Maine, do your homework and be prepared: Check the weather, dress accordingly for the season (and remember to always wear bright orange during hunting season), stay on the marked trails, carry out what you carried in, bring any hiking equipment that may be necessary to navigate your chosen route, and bring plenty of water, bug spray, and sunscreen.
Map of Portland-Area Day Hikes
Follow this map to explore the Maine outdoors.
The Summit Trail, Bradbury Mountain State Park
Bradbury Mountain State Park is open year-round and offers 18 mostly shared-use trails (hiking, biking, horseback)—and The Summit Trail is one of the most popular.
The trail is short, yes—but very steep, and employs several stone staircases along the way. Once at the top, you’ll enjoy breathtaking views of Casco Bay and Portland’s skyline—and if you still have some extra energy once you’ve taken in the sights, you can always go back down via the Bluff, Terrace, and Northern Loop Trails, which will add just under a mile to your trek.
Distance/drive time from downtown Portland: 23 miles/27 minutes
Length/type: .3 miles/out and back
Difficulty/Elevation gain: Moderate to intermediate (due to steepness)/196’
Trailhead address: 528 Hallowell Road, Pownal, ME 04069
Dog-friendly: Yes, leashed
Free or fee: Fee ($4 adult resident, $6 adult non-resident, $2 seniors)
Post-hike nosh: Jameson Tavern
The Pismire Bluff Trail, Raymond Community Forest
Owned by the Loon Echo Land Trust, The Raymond Community Forest’s small network of four trails includes this one, which must be accessed via The Spiller Homestead Loop.
The Bluff Trail offers a solid, challenging trek that rewards hikers with epic panoramas of Sebago Lake, Crescent Lake, and The White Mountains; on a clear day, you can see Mount Washington.
Some sections are quite steep, and there are stone steps in one area; this trail is one of two earmarked for hikers only.
Distance/drive time from downtown Portland: 30 miles/44 minutes
Length/type: 1.5 miles, out and back
Difficulty/Elevation gain: Moderate/452’
Trailhead parking address: 141 Conesca Rd, Raymond, ME 04071
Dog-friendly: Yes, leashed after 9 a.m.
Free or fee: Free (donations to the land trust are welcomed)
Post-hike nosh: Jess ‘n Nic’s Pizzeria & Pub
The Cedar to Goose Foot Trail, Mount Agamenticus
The well-loved network of 9 trails at the Mount Agamenticus Conservation Region allows hikers to enjoy the panoply of natural wonders that also happen to be home to the most diverse collection of flora and fauna in the state.
While a fair few of the trails begin and end at the base of “Mount Aggie,” this one begins at the summit and utilizes three other trails in its loop: Vulture’s View, Sweet Fern, and Goose Foot.
There are plenty of color-coded blazes so that you know which trail you’re following; note that some of the slabs of Vulture’s Trail are steep and can be very slippery in wet weather.
Construction is ongoing for new restrooms at the base and summit and should be completed in 2023; check the website for updates or closures.
Distance/drive time from downtown Portland: 50 miles/53 minutes
Length/type: 2.1 miles/loop
Difficulty/Elevation gain: Difficult/498’
Trailhead address: 111 Mountain Rd, Cape Neddick, ME 03902
Dog-friendly: Yes, leashed
Free or fee: Free
Post-hike nosh: Gravy
The Cliff Trail, Harpswell
Harpswell is one of those finger-like promontories that project southward off Route One; it is the perfect mini-representation of Maine’s abundant natural variety. Rocky cliffs, towering pines, rolling hills, and meandering shorelines…all of which you can enjoy on The Cliff Trail, part of which is wheelchair accessible; there is nearly a half-mile-long path at the beginning of the route that was widened in 2021 for this purpose.
The trail’s name is apt; you’ll see why when you reach its 150’ clifftop summit overlooking Long Reach. Beware of the abundance of roots along the way, but don’t look down so much that you miss the many fairy houses constructed along the trail (and feel free to add to this diminutive community).
Distance/drive time from downtown Portland: 35 miles/44 minutes
Length/type: 2.3 miles/loop
Difficulty/Elevation gain: Moderate/262’
Trailhead address: 263 Mountain Rd, Harpswell, ME 04079
Dog-friendly: Yes, leashed from 10 a.m. to 4 p.m.
Free or fee: Free
Post-hike nosh: Flight Deck Brewing
The White Trail, Fore River Sanctuary
Prefer to stay closer to the city without sacrificing the hike view factor? If so, then the Fore River Sanctuary is a great option. You’ll see Portland’s only natural waterfall—50’ Jewell Falls—and if you’re partial to birdwatching, keep your eyes peeled, especially around the estuary.
The trail is pretty much flat, especially along the portion that runs along the former Cumberland and Oxford Canal; you’ll encounter no more than a gentle incline here and there, and you’ll cross two boardwalks across the marshes as well as a bridge along the way. This is a great springtime hike, thanks to the abundance of wildflowers.
Distance/drive time from downtown Portland: 4 miles/13 minutes
Length/type: 3.3 miles/out and back
Difficulty/Elevation gain: Easy/177’
Trailhead address: Several trailheads; see trail link
Dog-friendly: Yes, leashed
Free or fee: Free
Post-hike nosh: The Great Lost Bear
Blue, Orange, and White Trails Loop, Blackstrap Hill Preserve
This predominantly-wooded, multi-use trail meanders along a river and several burbling brooks that can become true spectacles come winter melt; seasonal waterfalls are common.
Wildlife such as porcupines, deer, and beaver can be seen in the preserve as well as a host of feathered friends and amphibians; as most of this loop trail is under tree cover, most of the views afforded can be found while passing underneath the power lines.
Be sure to keep a sharp eye on the markers, as it is easy to miss some of them, and be alert for mountain bikers on this mixed-use trail.
Distance/drive time from downtown Portland: 10 miles/20 minutes
Length/type: 4.2 miles/loop
Difficulty/Elevation gain: Moderate/531’
Trailhead address: 369 Blackstrap Rd, Falmouth, ME 04105
Dog-friendly: Yes. Leashed within 300’ of trailhead; may be off-leash beyond if voice-controlled.
Free or fee: Free
Post-hike nosh: The Moose
The Ledges Trail, Pleasant Mountain
Another property owned by the Loon Echo Land Trust, this year-round gem is even more beautiful in the wintertime—but only if you have spikes, as the trail can be very icy, especially if the snow has been packed down.
This is the tallest mountain in the region and features a 10-mile trail network, including this one, which offers amazing views of Sebago Lake and the Presidential mountain range.
You’ll encounter lots of ledge, frequent switchbacks, and stone staircases, and while most of the trail is gently sloped, there are some steep spots, so take caution if conditions are wet.
Distance/drive time from downtown Portland: 45 miles/60 minutes
Length/type: 3.3 miles/out and back
Difficulty/Elevation gain: Moderate/1,512’
Trailhead address: 350 Mountain Rd, Denmark, ME 04022
Dog-friendly: Yes, leashed
Free or fee: Free (donations to the land trust are welcome)
Post-hike nosh: Campfire Grille
The Mount Cutler Trail, Mount Cutler Park & Conservation Area
Part of Mount Cutler’s five miles of trails, this loop affords hikers the right of way through tracts of private property as well as public.
To reach the rewarding panoramic views near the summit (the trail does not actually reach the summit, due to private property restrictions), you’ll have to tackle a few near-vertical scrambles, so make sure all of the members of your party—including any four-legged companions—are up to the challenge.
There are three scenic overlooks—the last of which offers the most expansive views—and you’ll be treated to sights like the Saco River and the White Mountains.
You’ll also want to bring along a trail map, as many hikers have reported difficulty following the red blazes.
Distance/drive time from downtown Portland: 38 miles/59 minutes
Length/type: 4.3 miles/loop
Difficulty/Elevation gain: Moderate to difficult/1,387’
Trailhead address: Hiram Hill Rd, Hiram, ME 04041 (parking on left, shortly after RR tracks)
Dog-friendly: Yes; may be off-leash only if voice-controlled.
The Libby Hill, Virginia, & Roscoe Trail Loop, The Lowell Preserve
Part of the Presumpscot Regional Land Trust, this multi-trail loop is part of a larger, year-round, 6-mile network that offers hiking for all skill levels—but this particular route leans toward moderately difficult, due to the technical aspects in the latter portion of the trail (narrow, steep, and rocky terrain).
All of the trails are exceptionally well-tended and include newly-constructed boardwalks and bridges over some of the streams and wet spots. The additional shorter trails are great opportunities for more energetic hikers to add more distance to their day.
A few of these trails are multi-use, so expect everything from horses, cross-country skiers, and mountain bikers to ATVs and snowmobiles to appear at any time.
Distance/drive time from downtown Portland: 12 miles/24 minutes
Length/type: 3.8 miles/loop
Difficulty/Elevation gain: Moderate to difficult/400’
Trailhead address: 47 Falmouth Rd, Windham, ME 04062 (at the fire station)
Dog-friendly: Yes
Free or fee: Free
Post-hike nosh: Cece’s Diner & Bar
The Blue & Yellow Trails, Burnt Meadow Mountain
One of the most popular trails on this list, you should expect to have a good amount of company on this hike.
If you are up for a challenge, take the Blue Trail to the peak of Burnt Meadow Mountain; you’ll enjoy rigorous scrambles and steep climbs on this route, which is the most direct to the top—but make sure you’re equipped for icy hiking in the winter.
The upside (sorry, couldn’t help myself) of getting the hard part over first is that the Yellow Trail is an easier—albeit longer—descent; the near-vertical rock faces on the Blue Trail make for an extremely tricky journey down.
The views at the top are worth the effort—especially on a clear day.
Distance/drive time from downtown Portland: 45 miles/70 minutes
Length/type: 3.4 miles/loop
Difficulty/Elevation gain: Moderate/1,404’
Trailhead address: 400 Spring St, Brownfield, ME 04010
Dog-friendly: Yes, leashed; allowed off-leash in a few spots
Free or fee: Free
Post-hike nosh: The Back Burner Restaurant
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