Portland Trails volunteers installing the bridge over Jewell Falls in Fore River Sanctuary, 1994.

Portland Trails is proud to have served Greater Portland, its residents, visitors, and neighbors for over 30 years!
Read through all we've accomplished together:


  • Portland Trails upgrades the trail behind PATHS & Casco Bay High School to byway standards, as part of the North Deering Bicycle Byway collaboration with the City of Portland.
  • Portland Trails holds the Trail to Prevail 10K, a virtual run/bike/walk challenge to raise money for Portland Trails during the COVID-19 pandemic.



  • Portland Trails celebrates it's 30th anniversary!
  • Lindsay Conrad is hired as Portland Trails' full-time Director of Development.



  • Portland Trails breaks ground on Clark Brook Trail, generously funded by the IDEXX Foundation.
  • Angelique Bitshilualua is hired as Portland Trails' first Inclusion Coordinator.
  • Kara Wooldrik steps down from her role as Executive Director after ten years.


  • Bayside Trail opens, connecting the downtown with Eastern Prom and Back Cove
  • Loring Memorial Trail opens at the top of the Eastern Promenade
  • Portland Trails' service learning program is launched



  • PT celebrates 20th anniversary
  • 10-mile crosstown Forest City Trail opens
  • Bridges to the Future Capital Campaign launched
  • Bayside Trail Capital Campaign meets goal
  • Portland Trails works with volunteers to plant 101 dogwood trees on Bayside Trail



  • Kara Wooldrik hired as Executive Director
  • Nan Cumming resigns as Executive Director
  • Sebago to the Sea Trail opens
  • The City of Portland acquires Canco Woods



  • First Portland Trails 15x15
  • Extension of Stroudwater Trail into Westbrook (to Spring Street)
  • Boyd Street Trail constructed
  • Formalized Canco Woods Trails
  • Upgraded bridges in the Presumpscot River Preserve
  • Extended the Midslope Trail from the Loring Memorial end of the Eastern Prom to Washington Avenue
  • Engaged neighborhoods in community meetings to set a vision for trails, conservation, active transportation and placemaking for the future



  • Co-led effort to establish Portland's first Open Streets project: Sundays on the Boulevard
  • Manages Nason's Corner playground project which is being completed in partnership with Breakwater School and City of Portland
  • Receives $18,000 grant from the Lerner Foundation that will be used to facilitate a public process to determine a shared vision for Portland's public, open and green spaces.



  • Portland Trails receives $75,000 grant from Jane's Trust for placemaking efforts in East Bayside.
  • Adopts new, inclusive mission and comprehensive 5-year strategic plan to guide future work.
  • Old Bug Light grant funds PT endowment and capacity building endeavors.
  • Grant funded projects begin on Fore River Trail to make Congress/Stroudwater area more accessible by bike.
  • New trail projects in Westbrook extend network and walking-biking infrastructure off-peninsula.



  • Portland Trails celebrates 25th Anniversary!
  • Placemaking efforts in East Bayside neighborhood include completion of the Gould St pocket park and very successful first annual cross city Scavenger Hunt with 80+ participants.
  • Portland Trails welcomes new Advancement Manager to build capacity into next 25 years of trails.
  • Numerous bridges replaced across network, including significant work in Presumpscot River Preserve.
  • River's Edge steps replaced on the Stroudwater Trail.
  • Expanding into Westbrook: Blue Spruce trail and walking trails on Conant Property completed officially open to public.
  • Maine Conservation Corps team collaborates with city and Portland Trails to improve habitat and soil quality and prevent erosion in Presumpscot River Preserve.



  • Portland Trails spearheads three neighborhood placemaking projects in Knightville, South Portland, Libbytown and the West End, Portland.
  • Significant repairs are made on heavily used trails including the Stroudwater Trail and Presumpscot River Preserve.
  • Portland Trails teams with the Maine Conservation Corps for a second year in a row. This year, funded by the City of Portland, Portland Trails leads the crew in updating and formalizing trails through and around PATHS High School.
  • Portland Trails helps rebuild trails in Evergreen Cemetery and near the Brentwood Community Gardens, following municipal forestry work.
  • Grant-funded conservation work begins on Brickyard Point and Berle Mile Pond properties.





  • Portland Trails holds the 20th annual Trail to Ale 10K!
  • Funded by an AARP grant, Portland Trails upgrades Canco Woods trails to be more accessible for the neighbors in the adjacent senior housing. Depending on seasonal conditions, it is now possible for people using wheelchairs, walkers, strollers, and bicycles to enjoy a loop through the woods.


  • Connector between Eastern Prom and Back Cove Trails built
  • Stroudwater Trail extended
  • Fore River Trail, phase 1, begun and finished
  • Armillary Sphere sculpture installed at the head of the Eastern Prom Trail
  • 1st annual Portland Trails 10K race


  • Portland Trails 10th Anniversary!
  • Portland Trails launches first major capital campaign to help City of Portland acquire 48 acres along the Presumpscot River, creating the Presumpscot River Preserve
  • PT’s co-founder Tom Jewell inaugurates his annual 10-mile guided Walk Across the Forest City, offered free of charge to the public
  • Planning for Bayside Trails and open spaces begun


  • Capital campaign to fund purchase of 9.5 more acres of Presumpscot River land for the Preserve Hall Elementary School Trail begun
  • Lyseth School Trail extended
  • Collaboration with Stroudwater Village Association to preserve “Corner” parcel of open space Portland Trails inaugurates the Senior Strolls, a series of guided educational trail walks First edition Portland Trails Map and Trail Guide published


  • Trails within the Presumpscot River Preserve begun
  • I-295 Connector Trail begun
  • Capisic and Fore River Trails connected by Frost Street
  • Planning for Thompson’s Point Trail


  • Presumpscot River Preserve expanded to 57.5 acres; trails extended north and south along the river Corporate Adopt-a-Trail sponsorship program initiated


  • Jaime Parker hired as full-time Trails Manager
  • Thompson’s Point Trail planned
  • Jewell Falls access trail rebuilt
  • Outside Magazine and Vegetarian Times each credit Portland Trails with making Portland a great place to live and play
  • Portland Trails Map and Trail Guide, second edition, published
  • Alix Hopkins, former Executive Director, writes “Groundswell: Saving Places, Finding Community” (published by the Trust for Public Land )
  • First land acquisition in Westbrook, 4 acre parcel on Presumpscot River


  • Brickyard Point acquired; trail roughed out
  • Capisic Pond Park expanded
  • Trails begun on Presumpscot River , Westbrook
  • Planning for Bayside Trail renews with City aquisition of rail right of way
  • Starbird Lane Trail built
  • Boat Launch built on Presumscot River , Rte 302
  • Thompson’s Point Trail connected to the Portland Transportation Center
  • Weekly summer 5K run around Back Cove inaugurated in partnership with Maine Running Company
  • Popular Senior Strolls series expanded and renamed as the Discovery Treks


  • Fore River Sanctuary (85 contiguous acres) acquired from Maine Audubon
  • Thompson’s Point Trail landscaped and lengthened
  • Brickyard Point Trail begun; plans made for its connection to the Tidewater Trail
  • Jack Path on Munjoy Hill formalized into an official trail.


  • PT cofounder Tom Jewell awarded L.L. Bean’s Outdoor Hero Award
  • Fort Sumner Park Trail opened on Munjoy Hill, linking North Street with Washington Avenue
  • Portland Trails Map and Guide, third edition, published
  • Fore River Sanctuary improved with new signage and foot bridges
  • Web site named by American Trail as the “Best Community Trails System Site”
  • Facebook page launched


  • Fort Allen Park Trail opening, linking the Eastern Prom Trail to Fort Allen Munjoy Hill
  • PT wins “Environmental Hero Award” from Portland Indie Biz voters
  • GIS mapping of trail system begun
  • Planned Giving Program, “Leave a Trail,” is launched


      • Nathan Smith becomes the first President of the infant Portland Trails, organized out of the Portland Shoreway Access Coalition to advocate for a connected trail system Portland Trails creates a “Vision Map” to share the trail network idea.



      • Donna Larson becomes PT’s first (part-time) Executive Director
      • Back Cove’s 3.6 miles grandfathered into the Portland Trails system



      • Alix Hopkins hired as full-time Executive Director
      • Capisic Pond Trail begun
      • Permitting for the Fore River Trail begun



      • Capisic Pond Trail completed Jewell Falls donated by the Jewell family
      • Portland Trails helps the City of Portland get federal funding to acquire 30-acre parcel along Eastern Prom
      • Bridge over Jewell Falls funded



      • Bridge across Fore River in Maine Audubon’s Fore River Sanctuary funded
      • Stroudwater Trail - eight acres along river donated Portland Trails voted the “Most Effective Citizens Group” by readers of Casco Bay Weekly newspaper



      • Fore River Bridge installed in the Fore River Sanctuary
      • Plans for Eastern Prom Trail sent to City Council
      • Portland Trails voted the “Most Effective Citizens Group” by readers of Casco Bay Weekly newspaper for the second year in a row



      • Eastern Prom Trail groundbreaking Julie N oil tanker accident spills 200,000 gallons of oil into Portland Harbor;
      • Portland Trails awarded funds to restore Fore River shoreline and build Fore River Trail



      • UNUM grants easement for Stroudwater Trail
      • Stroudwater Trail begun Eastern Prom Trail Phase 1 completed;
      • Phase 2 begun www.trails.org goes live



      • Eastern Prom Trail completed



      • Lyseth School Trail built
      • Fore River Trail begun
      • Riverton Trolley Park Trail begun
      • Alix Hopkins resigns as Executive Director
      • Nan Cumming hired as Executive Director


  • Forest City Land Trust formed by Portland native and lawyer Tom Jewell.



  • Portland City Hall convenes a workshop to develop the Shoreway Access Plan. During a stretch-break in the hallway, attendees Tom Jewell, Nathan Smith, Dick Spencer, and Cathy Stivers form the Portland Shoreway Access Coalition.