In the spring of 2020, I set out to hike the 37 Portland Trails with my two boys. We did this as a way of providing adventure and nature therapy during the COVID-19 pandemic. We soon branched out to other land trusts in Greater Portland, amazed by the endless hikes available so close to home. I began sharing details about these hikes through a weekly newsletter and created a trail challenge where kids would search for little clay figures, called “Seek’ems,” which I hid on trails throughout Southern Maine. Through this project, I learned that the quest for Seek’ems inspired kids to explore new trails each week, and once there, they created their own fun. I also learned that beauty can be found in our backyards and that hiking is for any season, any age, and any ability.
Although I no longer hide Seek’ems, I’ve discovered many trails with features your kids will love. Here are some of my favorites. To access the full list of trails, visit my website at www.outdoormovementproject.com.
Enjoy your time outdoors!
Jill McMahon
Outdoor Movement Project
Emmons Preserve, Kennebunkport
In addition to the gorgeous trails and woods along the Batson River on this property, there is a wheelchair and stroller-accessible Community Labyrinth, designed in the same 7-circuit pattern found on ancient archeological sites. From early December through January 6th, the path is lit by solar lights after dusk for the holiday season.
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Morse Mountain to Seawall Beach, Phippsburg
Located within the Bates-Morse Mountain Conservation Area, this 4-mile out-and-back hike is among the most stunning in midcoast Maine. The 600-acre preserve features salt marshes, pine forests, and rivers that lead to a two-mile stretch of white sand beach, where your kids will play for hours.
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Saco Heath Preserve, Saco
A visual work of art that includes a one-mile, multicolored accessible boardwalk for all ages and abilities, including a short woods loop at the end of the boardwalk.
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Swinging Bridge Park & River Walk, Brunswick
Just outside of charming downtown Brunswick is a historic swinging bridge leading to a flat, accessible paved trail along the Androscoggin River.
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The Wiggly Bridge & Steedman Woods, York
This miniature suspension bridge, built in 1936, carries you across the tidal flow from the pond to the river. A man-made causeway leads to the bridge, which continues onto the short, looping wooded path with a storybook trail in Steedman Woods. The Wiggly Bridge is the smallest suspension bridge in the U.S. and possibly the world!
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Shaw Cherry Hill Farm, Gorham
This 258-acre, public recreational area includes a large parking lot, seven trails, an ice skating pond, a children’s storybook walk, and access to the Presumpscot River for hand-carrying kayaks and canoes. This is a great place for biking, especially for those early bikers, since the trails are wide and mostly flat.
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Spears Hill Trail & Broad Cove Reserve, Cumberland
Broad Cove Reserve is one of the few special places along the Maine coast where horseshoe crabs come to lay their eggs from mid-May to mid-June. It is also a gorgeous little stretch of beach on 104 acres, including woods and trails.
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Timber Point Trail, Biddeford
This flat, 1.4-mile out-and-back trail is great for all ages. It includes just about everything: rocky coastlines, sheltered coves, tidepools, island access, and historic buildings.
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Donnabeth Lippman Park, Windham
Formerly known as the Chaffin Pond Preserve, this 123-acre wooded area includes a 1.5-mile loop around a 10-acre pond, including a playground and picnic tables. The dirt trail is flat, and this trail is listed as ADA Accessible. It’s a family-friendly affair over here.
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Mount Apatite, Auburn
These 325 acres of woods include 7.6 miles of trails linking abandoned quarries, steep ledges, and large boulders. Gem-quality tourmaline was first discovered here over 150 years ago. Since then, commercial and amateur mineral explorers have come to this spot to find apatite, tourmaline, and quartz – an activity called rockhounding, which your kids will love.
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Tryon Mountain, Pownal
If your kids like Minecraft, they’ll love this short hike. The 0.5-mile out-and-back trail leads to a historic feldspar quarry and is lined with shiny, sparkly rocks – another great spot for rockhounding.
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Pride Preserve, Westbrook
The Pride Preserve opened in 2020 and is the largest conserved forestland in greater Portland. It includes 188 acres and 3.5 miles of trails with at least 11 gnome homes tucked along the sides of the path – a built-in treasure hunt!
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Dow’s Woods, South Portland
A short, storybook loop near a 2-acre pond filled with the sweet sound of bullfrogs. This is a perfect spot for the youngest of hikers.
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Fore River Sanctuary, Portland
An 85-acre preserve with 5.6 miles of trails encompassing some of the most diverse habitats in Portland. It is also home to Jewell Falls, Portland’s only natural waterfall.
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Crescent Beach Trail, Cape Elizabeth
This trail leads through forest, open meadow, an old apple orchard, a pond, and a beach with red sand. The red-sand cove, called Jordan Point, is located at the western end of Crescent Beach State Park. This sweet spot is separated from the larger beach by a rocky ledge, so you’d never know it was there.
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By Jill McMahon of the Outdoor Movement Project (pictured, far-left).
Jill’s passion for outdoor recreation began in her childhood and grew during her college years through hiking in Colorado, Western Massachusetts, and California, along with a transformative Outward Bound course at Hurricane Island in Maine. Since launching Outdoor Movement Project in 2014, she has created programs that engage kids in enjoyable outdoor activities such as bike clubs, running clubs, summer camps, trail challenges, and the outdoor after-school program “OMP Camp.” With her kids now older, OMP aims to inspire individuals of all ages and abilities to embrace the outdoors. In 2022, Jill published a trail guide featuring 100 hikes in Southern Maine and is currently working on a second guide focused on dog-friendly hikes in New England. She shares insights on hikes of all kinds through her Substack newsletter.
Discover the Trails in Your Own Backyard
In her beautifully photographed guide to 100 trails in Southern Maine, Jill McMahon reminds us that you don’t have to go far to experience the joy of the outdoors. Whether you’re brand new to hiking or looking for your next family-friendly trail, this book offers something for every season, every ability, and every age.
Rooted in her own explorations with family, friends, and her dog, Jill’s trail descriptions go beyond logistics to highlight the simple, powerful moments that nature makes possible. Each hike includes useful details like distance, difficulty, accessibility, and whether dogs are welcome—plus full-color photos and historical tidbits that bring each path to life.
This guide is more than a collection of hikes—it’s an invitation to explore local trails with curiosity, confidence, and a sense of wonder. Whether you’re lacing up for a weekend walk or building lifelong habits of outdoor play with your kids, you’ll find inspiration on every page.
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