Winthrop, ME Trails and Maps

73 Reviews

Looking for the best trails around Winthrop?

Find the top rated trails in Winthrop, whether you're looking an easy walking path or a long bike trail, you'll find what you're looking for. Click on a trail below to find trail descriptions, trail maps, photos, and reviews.

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Activities
Length
Surfaces
Type
17 Results
Activities
Length
Surfaces
Type

Auburn Riverwalk

1.6 mi
State: ME
Asphalt, Brick, Crushed Stone, Gravel

Back Cove Trail

3.6 mi
State: ME
Asphalt

Bayside Trail

1 mi
State: ME
Asphalt

Belfast Rail Trail on the Passagassawaukeag

2.3 mi
State: ME
Crushed Stone, Gravel

Eastern Promenade Trail

2.1 mi
State: ME
Asphalt

Eastern Trail

28.9 mi
State: ME
Asphalt, Crushed Stone, Sand

Fore River Parkway Trail

2.6 mi
State: ME
Asphalt

Kennebec River Rail Trail

6.5 mi
State: ME
Asphalt

Kennebec Valley Trail

14.5 mi
State: ME
Crushed Stone, Dirt, Sand

Mountain Division Trail

9.7 mi
State: ME
Asphalt, Gravel

Old Narrow Gauge Volunteer Trail

1.25 mi
State: ME
Ballast, Dirt

Papermill Trail

4 mi
State: ME
Asphalt

Riverton Rail Trail

1.5 mi
State: ME
Concrete, Dirt, Sand

Rotary Centennial Trail

1.5 mi
State: ME
Crushed Stone, Dirt, Grass

WW&F Narrow Gauge Trail

0.68 mi
State: ME
Dirt, Grass

Whistle Stop Rail-Trail

15.8 mi
State: ME
Dirt, Gravel, Sand

Whitman Spring Road Trail

2 mi
State: ME
Gravel
Trail Image Trail Name States Length Surface Rating
The Auburn Riverwalk passes through the heart of the old mill district of the Twin Cities of Auburn and Lewiston. The 1.6-mile paved and gravel path offers many scenic views of the Androscoggin River,...
ME 1.6 mi Asphalt, Brick, Crushed Stone, Gravel
The paved Back Cove Trail rings its namesake tidal basin and offers lovely views of the Portland skyline. You also might spot great blue herons or other birds along the tree-lined waterfront. A...
ME 3.6 mi Asphalt
Portland’s Bayside Trail packs a lot into its 1-mile length. The paved pathway provides a pleasant route between commercial and residential areas in the Bayside and East Bayside neighborhoods. Once an...
ME 1 mi Asphalt
Visitors to the Belfast Rail Trail on the Passagassawaukeag (pronounced pas-uh-gas-uh-WAH-keg and conveniently shortened to Passy Rail Trail by locals) can see vintage trains at one end of the trail...
ME 2.3 mi Crushed Stone, Gravel
Old salts should love the Eastern Promenade Trail, as it skirts the shoreline of Portland’s Casco Bay and Portland Harbor. The 2.1-mile paved trail is always within sight of the water and is one of...
ME 2.1 mi Asphalt
The 28.9-mile Eastern Trail connects the historic towns along Maine’s southern coast from the woods near Kennebunk to South Portland’s harbor lighthouse. Nearly 22 miles of the route follows off-road...
ME 28.9 mi Asphalt, Crushed Stone, Sand
Portland’s Fore River Parkway Trail provides an important transportation link in the community while at the same time offering sweeping views of the Fore River. At the north end of the trail, you’ll...
ME 2.6 mi Asphalt
Visitors to the 6.5-mile-long Kennebec River Rail Trail mostly stay within sight of the wide river as the paved trail links the state capital of Augusta with the river towns of Hallowell, Farmingdale,...
ME 6.5 mi Asphalt
Keep your ears open for the haunting call of loons along the scenic Kennebec Valley Trail. They’re just one example of the wildlife—another is the moose—that inhabits the river, woods, and fields...
ME 14.5 mi Crushed Stone, Dirt, Sand
The Mountain Division Trail exists as two separate segments of what will eventually be a more than 50-mile-long trail from Fryeburg to Portland. The southern section rolls for about 6 miles between...
ME 9.7 mi Asphalt, Gravel
The Old Narrow Gauge Volunteer Trail occupies a portion of the old Kennebec Central Railroad right-of-way in the town of Randolph, ME. As of 2012, the trail runs for 1.25 miles between Water Street in...
ME 1.25 mi Ballast, Dirt
The Papermill Trail celebrates the heritage of mills in the development of the town of Lisbon and the surrounding area while providing an easy, pleasant trail experience for users of all abilities....
ME 4 mi Asphalt
The scenic Riverton Rail Trail—also known as “Sandy Road” by residents of Portland’s Riverton neighborhood—follows the former corridor of the Portland-Lewiston Interurban Railroad, which stopped...
ME 1.5 mi Concrete, Dirt, Sand
The Rotary Centennial Trail crosses two towns—Benton and Winslow—in central Maine, about 50 miles southwest of Bangor. The scenic wooded trail follows a former rail bed along the eastern shore of the...
ME 1.5 mi Crushed Stone, Dirt, Grass
Owned and actively maintained by the Wiscasset, Waterville, and Farmington Railway museum, this trail meanders along the currently disused railroad right of way through the Town of Alna in the village...
ME 0.68 mi Dirt, Grass
A former Maine Central Railroad line provides a year-round playground for motorized and nonmotorized trail users to explore the western hills of Maine. The long, flat, mostly straight stretches of the...
ME 15.8 mi Dirt, Gravel, Sand
The trail sits on the northwestern shore of Lake Auburn. A former roadway, the wide gravel path can accommodate various kinds of uses including, running, biking, walking dogs. And in the winter, the...
ME 2 mi Gravel

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Trails by activity

Auburn Riverwalk

ME - 1.6 miles

The Auburn Riverwalk passes through the heart of the old mill district of the Twin Cities of Auburn and Lewiston. The 1.6-mile paved and gravel path offers many scenic views of the Androscoggin River,...

Fore River Parkway Trail

ME - 2.6 miles

Portland’s Fore River Parkway Trail provides an important transportation link in the community while at the same time offering sweeping views of the Fore River. At the north end of the trail, you’ll...

Kennebec River Rail Trail

ME - 6.5 miles

Visitors to the 6.5-mile-long Kennebec River Rail Trail mostly stay within sight of the wide river as the paved trail links the state capital of Augusta with the river towns of Hallowell, Farmingdale,...

Back Cove Trail

ME - 3.6 miles

The paved Back Cove Trail rings its namesake tidal basin and offers lovely views of the Portland skyline. You also might spot great blue herons or other birds along the tree-lined waterfront. A...

Accordion

Mountain Division Trail

ME - 9.7 miles

The Mountain Division Trail exists as two separate segments of what will eventually be a more than 50-mile-long trail from Fryeburg to Portland. The southern section rolls for about 6 miles between...

Bayside Trail

ME - 1 miles

Portland’s Bayside Trail packs a lot into its 1-mile length. The paved pathway provides a pleasant route between commercial and residential areas in the Bayside and East Bayside neighborhoods. Once an...

Eastern Promenade Trail

ME - 2.1 miles

Old salts should love the Eastern Promenade Trail, as it skirts the shoreline of Portland’s Casco Bay and Portland Harbor. The 2.1-mile paved trail is always within sight of the water and is one of...

Papermill Trail

ME - 4 miles

The Papermill Trail celebrates the heritage of mills in the development of the town of Lisbon and the surrounding area while providing an easy, pleasant trail experience for users of all abilities....

Old Narrow Gauge Volunteer Trail

ME - 1.25 miles

The Old Narrow Gauge Volunteer Trail occupies a portion of the old Kennebec Central Railroad right-of-way in the town of Randolph, ME. As of 2012, the trail runs for 1.25 miles between Water Street in...

Riverton Rail Trail

ME - 1.5 miles

The scenic Riverton Rail Trail—also known as “Sandy Road” by residents of Portland’s Riverton neighborhood—follows the former corridor of the Portland-Lewiston Interurban Railroad, which stopped...

Rotary Centennial Trail

ME - 1.5 miles

The Rotary Centennial Trail crosses two towns—Benton and Winslow—in central Maine, about 50 miles southwest of Bangor. The scenic wooded trail follows a former rail bed along the eastern shore of the...

Whitman Spring Road Trail

ME - 2 miles

The trail sits on the northwestern shore of Lake Auburn. A former roadway, the wide gravel path can accommodate various kinds of uses including, running, biking, walking dogs. And in the winter, the...

Eastern Trail

ME - 28.9 miles

The 28.9-mile Eastern Trail connects the historic towns along Maine’s southern coast from the woods near Kennebunk to South Portland’s harbor lighthouse. Nearly 22 miles of the route follows off-road...

Kennebec River Rail Trail

ME - 6.5 miles

Visitors to the 6.5-mile-long Kennebec River Rail Trail mostly stay within sight of the wide river as the paved trail links the state capital of Augusta with the river towns of Hallowell, Farmingdale,...

Old Narrow Gauge Volunteer Trail

ME - 1.25 miles

The Old Narrow Gauge Volunteer Trail occupies a portion of the old Kennebec Central Railroad right-of-way in the town of Randolph, ME. As of 2012, the trail runs for 1.25 miles between Water Street in...

Kennebec Valley Trail

ME - 14.5 miles

Keep your ears open for the haunting call of loons along the scenic Kennebec Valley Trail. They’re just one example of the wildlife—another is the moose—that inhabits the river, woods, and fields...

Mountain Division Trail

ME - 9.7 miles

The Mountain Division Trail exists as two separate segments of what will eventually be a more than 50-mile-long trail from Fryeburg to Portland. The southern section rolls for about 6 miles between...

Accordion

Bayside Trail

ME - 1 miles

Portland’s Bayside Trail packs a lot into its 1-mile length. The paved pathway provides a pleasant route between commercial and residential areas in the Bayside and East Bayside neighborhoods. Once an...

Back Cove Trail

ME - 3.6 miles

The paved Back Cove Trail rings its namesake tidal basin and offers lovely views of the Portland skyline. You also might spot great blue herons or other birds along the tree-lined waterfront. A...

Papermill Trail

ME - 4 miles

The Papermill Trail celebrates the heritage of mills in the development of the town of Lisbon and the surrounding area while providing an easy, pleasant trail experience for users of all abilities....

Eastern Trail

ME - 28.9 miles

The 28.9-mile Eastern Trail connects the historic towns along Maine’s southern coast from the woods near Kennebunk to South Portland’s harbor lighthouse. Nearly 22 miles of the route follows off-road...

Whitman Spring Road Trail

ME - 2 miles

The trail sits on the northwestern shore of Lake Auburn. A former roadway, the wide gravel path can accommodate various kinds of uses including, running, biking, walking dogs. And in the winter, the...

Riverton Rail Trail

ME - 1.5 miles

The scenic Riverton Rail Trail—also known as “Sandy Road” by residents of Portland’s Riverton neighborhood—follows the former corridor of the Portland-Lewiston Interurban Railroad, which stopped...

Whistle Stop Rail-Trail

ME - 15.8 miles

A former Maine Central Railroad line provides a year-round playground for motorized and nonmotorized trail users to explore the western hills of Maine. The long, flat, mostly straight stretches of the...

Fore River Parkway Trail

ME - 2.6 miles

Portland’s Fore River Parkway Trail provides an important transportation link in the community while at the same time offering sweeping views of the Fore River. At the north end of the trail, you’ll...

WW&F Narrow Gauge Trail

ME - 0.68 miles

Owned and actively maintained by the Wiscasset, Waterville, and Farmington Railway museum, this trail meanders along the currently disused railroad right of way through the Town of Alna in the village...

Auburn Riverwalk

ME - 1.6 miles

The Auburn Riverwalk passes through the heart of the old mill district of the Twin Cities of Auburn and Lewiston. The 1.6-mile paved and gravel path offers many scenic views of the Androscoggin River,...

Rotary Centennial Trail

ME - 1.5 miles

The Rotary Centennial Trail crosses two towns—Benton and Winslow—in central Maine, about 50 miles southwest of Bangor. The scenic wooded trail follows a former rail bed along the eastern shore of the...

Belfast Rail Trail on the Passagassawaukeag

ME - 2.3 miles

Visitors to the Belfast Rail Trail on the Passagassawaukeag (pronounced pas-uh-gas-uh-WAH-keg and conveniently shortened to Passy Rail Trail by locals) can see vintage trains at one end of the trail...

Eastern Promenade Trail

ME - 2.1 miles

Old salts should love the Eastern Promenade Trail, as it skirts the shoreline of Portland’s Casco Bay and Portland Harbor. The 2.1-mile paved trail is always within sight of the water and is one of...

Auburn Riverwalk

ME - 1.6 miles

The Auburn Riverwalk passes through the heart of the old mill district of the Twin Cities of Auburn and Lewiston. The 1.6-mile paved and gravel path offers many scenic views of the Androscoggin River,...

Old Narrow Gauge Volunteer Trail

ME - 1.25 miles

The Old Narrow Gauge Volunteer Trail occupies a portion of the old Kennebec Central Railroad right-of-way in the town of Randolph, ME. As of 2012, the trail runs for 1.25 miles between Water Street in...

Kennebec Valley Trail

ME - 14.5 miles

Keep your ears open for the haunting call of loons along the scenic Kennebec Valley Trail. They’re just one example of the wildlife—another is the moose—that inhabits the river, woods, and fields...

Belfast Rail Trail on the Passagassawaukeag

ME - 2.3 miles

Visitors to the Belfast Rail Trail on the Passagassawaukeag (pronounced pas-uh-gas-uh-WAH-keg and conveniently shortened to Passy Rail Trail by locals) can see vintage trains at one end of the trail...

Accordion

Kennebec River Rail Trail

ME - 6.5 miles

Visitors to the 6.5-mile-long Kennebec River Rail Trail mostly stay within sight of the wide river as the paved trail links the state capital of Augusta with the river towns of Hallowell, Farmingdale,...

Eastern Promenade Trail

ME - 2.1 miles

Old salts should love the Eastern Promenade Trail, as it skirts the shoreline of Portland’s Casco Bay and Portland Harbor. The 2.1-mile paved trail is always within sight of the water and is one of...

Riverton Rail Trail

ME - 1.5 miles

The scenic Riverton Rail Trail—also known as “Sandy Road” by residents of Portland’s Riverton neighborhood—follows the former corridor of the Portland-Lewiston Interurban Railroad, which stopped...

Back Cove Trail

ME - 3.6 miles

The paved Back Cove Trail rings its namesake tidal basin and offers lovely views of the Portland skyline. You also might spot great blue herons or other birds along the tree-lined waterfront. A...

Fore River Parkway Trail

ME - 2.6 miles

Portland’s Fore River Parkway Trail provides an important transportation link in the community while at the same time offering sweeping views of the Fore River. At the north end of the trail, you’ll...

Papermill Trail

ME - 4 miles

The Papermill Trail celebrates the heritage of mills in the development of the town of Lisbon and the surrounding area while providing an easy, pleasant trail experience for users of all abilities....

Rotary Centennial Trail

ME - 1.5 miles

The Rotary Centennial Trail crosses two towns—Benton and Winslow—in central Maine, about 50 miles southwest of Bangor. The scenic wooded trail follows a former rail bed along the eastern shore of the...

Eastern Trail

ME - 28.9 miles

The 28.9-mile Eastern Trail connects the historic towns along Maine’s southern coast from the woods near Kennebunk to South Portland’s harbor lighthouse. Nearly 22 miles of the route follows off-road...

Mountain Division Trail

ME - 9.7 miles

The Mountain Division Trail exists as two separate segments of what will eventually be a more than 50-mile-long trail from Fryeburg to Portland. The southern section rolls for about 6 miles between...

Bayside Trail

ME - 1 miles

Portland’s Bayside Trail packs a lot into its 1-mile length. The paved pathway provides a pleasant route between commercial and residential areas in the Bayside and East Bayside neighborhoods. Once an...

Whistle Stop Rail-Trail

ME - 15.8 miles

A former Maine Central Railroad line provides a year-round playground for motorized and nonmotorized trail users to explore the western hills of Maine. The long, flat, mostly straight stretches of the...

Whitman Spring Road Trail

ME - 2 miles

The trail sits on the northwestern shore of Lake Auburn. A former roadway, the wide gravel path can accommodate various kinds of uses including, running, biking, walking dogs. And in the winter, the...

WW&F Narrow Gauge Trail

ME - 0.68 miles

Owned and actively maintained by the Wiscasset, Waterville, and Farmington Railway museum, this trail meanders along the currently disused railroad right of way through the Town of Alna in the village...

Recent Trail Reviews

Eastern Trail

Try to avoid Biddeford

October, 2018 by shrink

Most of this trail is over packed earth, which is satisfactory, except following rain. The 4.5+ miles through Biddeford are poorly marked (download a map) and often hazardous. Scarborough marsh is beautiful and the rest of the trail is pleasant, often scenic. I rode the entire trail north one day and south the next. If I were to do it again, I would cut it into two smaller trails, and avoid Biddeford.

Eastern Trail

Variety is king on this trail

September, 2018 by robert.richter89

I rode the entire trail starting at Bug Light Park in South Portland and ending at Kennebunk; roughly 30 miles each way. I knew about the on road gaps and found them to be a positive as it added variety to the trail. The on road sections are fairly well marked and I only had an issue finding my way through Biddeford. The shoulders are very wide and I must say I found Maine drivers to be very courteous to me at every road crossing.

The off road sections of the trail are very well marked, shaded and very flat. I rode through forests and marshes and around residential neighborhoods. There is a fundraising effort to close one of the on road gaps on this trail. If that gap is closed I would give this trail five stars. I still highly recommend this trail as you can have a nice ride no matter what section you chose to ride.

Whistle Stop Rail-Trail

awsome for atv bike and walking. people are great and welcoming.

August, 2018 by jmes1979

awsome for atv bike and walking. people are great and welcoming.

Accordion

Whistle Stop Rail-Trail

Trail for Fat Tyre Bikes

August, 2018 by andysmthrs

I rode this trail on 20/8/2018. It was a beautiful day and the trail was dry. Having read the warnings about the sandy sections of the trail I took my mountain bike with 650B /2.20 tyres, thinking it would be sufficient. For 11 miles of the trail it was, but I struggled on the sandy sections in Jay, with the front end wanting to wash out as it hit the deeper berms. My fat tyre bike would have sailed through these sections, and should I ride the trail again It is what I would use.
On a hot day the shade of the trees along most of the route was very welcome. I rode from Livermore Falls to Farmington, and then back again, stopping for a quick lunch at the small country store in Wilton village: Where it is very pleasant to sit by the river on the provided benches and tables. The trip took me a little over three hours, the trail being better at the Farmington end, and becoming quite rough nearer the Livermore Falls end.
The guidebook says this is primarily an ATV/snowmobile trail and I think that is a correct summation. It is not a bicycle friendly trail, being too rough and the sand making it all but impossible for anything other than wide tyres

Eastern Trail

great after work bike ride

August, 2018 by mailtojanah

the first 6 miles was somewhat boring, just a dirt path in the woods but the remaining trail to Saco was fun weaving through neighborhoods and Saco river crossing was cool. excited to do the second section :)

Eastern Trail

First time and loved it,

June, 2018 by mayor1

My 9 year old and I found this and loved it. We started at Kennebunk Elementary, which was easy to find, and went about 5 miles. The trail has a very nominal and unnoticeable grade. The trail is shaded and has numerous small bridges crossing streams. It’s a beautiful and easy ride.

Kennebec River Rail Trail

Great First Ride

August, 2017 by mcwpage8

My husband and I just both got bikes and were at a family outing the day before in Augusta and decided to try out the trail. It was a beautiful trail and a great first ride. We will definitely be back!

Kennebec Valley Trail

Bingham area section

August, 2017 by tedmcgarry

Visiting Maine in August we found no place to rent bikes within 80 miles of the Trail. We decided to hike the section from Bingham south as we like free flowing rivers, not lakes behind dams. First issue was the Bingham Goodrich Rd trailhead. It is in the woods and out of sight from US 201 or houses. We chose to park at a more publicly visible location at a Supermarket across from North Country Rivers Outfitters where the Trail crosses a corner of the Outfitters property. We did get permission from the Supermarket and recommend parking here, not the Goodrich Rd. trailhead.

Second, the main issue for us was the Trail. This included the lack of views of this section of the river being obscured by Summer vegetation, the condition of the trail with muddy potholes and lack of a gravel surface and the permitted use of the Trail by ATV’s. The ATV drivers were respectful of hikers and slowed for us, but the vehicles were still noisy and created dust. We terminated the hike early and had ice cream at Here’s the Scoop in Bingham, sitting quietly on the bank of the Kennebec.

Headed south on US 201 to Arnolds Landing where the trail crosses the Kennebec. The trail is on the river bank and would have provided better water views had we hiked this section. Had to leave, as it is a slow drive from I-95. In summary, the Bingham area portion of the Trail would rank as our worst RTT experience from Maine to Virginia. We would not return even for ice cream on the river bank.

Papermill Trail

Local guide

June, 2017 by dubekaren7

I love this trail. Its quiet. Along river. Can here the wildlife. All ages out and about. Biking. walking. jogging. strollers. Next to a dairy joy👍

Mountain Division Trail

x country skiing

January, 2017 by mlibbyrn

So 15 degree weather does not stop us!
Started at otter pond and skied to Gambo Field.
Beautiful blue sky and crisp air. Maine the way it should be. Met a few snowmobiles and only a few other brave walkers. I love this trail and feel so blessed to be able to walk out the door and have this great place to play.

Belfast Rail Trail on the Passagassawaukeag

five stars is right!

October, 2016 by mike hurley

a wonderful thing about this trail is that it is handicapped accessible from the outer High Street parking lot in particular. The stone dust surface is impervious to wheels and motor driven and otherwise propelled wheel chairs are very easy to use on the trail.

That said... the trail is a wonder. There are three parking area access points. 1. downtown/intown where it intersects the Armistice Bridge walking bridge and Harbor Walk, 2. Upper Bridge (on High Street) and 3. out at the The Brooks Preservation railroad yard, station, and museum.

It is a remarkable 2.2 miles of natural world.

Belfast Rail Trail on the Passagassawaukeag

Excellent trail with great views

October, 2016 by aeljarou

The trail is beautifully groomed and hugs the Passagassawakeag river for over 2 miles. We started at the north end (13 Oak Hill Road) of the trail by the rail yard. The parking lot was packed when we got there as the excursion train was getting ready to leave. They have rides Saturdays and Sundays at 1 PM. The trains travel north from the parking lot and the trail goes south. The trail surface is perfect for walking and biking. It is treelined and has many small bridges that carry you over creeks. It took us 45 minutes of walking to get to the southern end at the intersection of Pierce St. and Front St. in Belfast. There is now a trailhead with a small parking lot at the southern end (not listed in the description). The trail connects there to the Belfast Harbor Walk which is an awesome urban trail through Belfast harbor and Front Street shipyard with a long pedestrian bridge across the Passagassawakeag.

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