Portland Trails is proud to have served Greater Portland, its residents, visitors and communities for 25 years.


  • 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 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 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.


  • 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.


  • First Portland Trails 15×15
  • 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


  • 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


  • 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


  • 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


      • 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 Trail 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.