WHERE TRAILS
BECOME
CAREER PATHS

Hourly rate - starting at $17 an hour, pay commensurate with experience. Day rate for days in field.

Our Mission is to be the leading center for climbing, adventure, and good living in southern Maine. We strive to serve our community by always reflecting the core values of the outdoors world.

Position Overview Position Description: Instructors work together with the Camp Director/Coordinator to plan and implement adventures for their campers.  Inside-Out: Our hybrid camps feature indoor and outdoor activities during day camp. Campers will range in age from 11-14.  Summit Leadership: Our Leadership Camps are week-long camps that focus on indoor climbing skills,...

$30/hour

The Bicycle Coalition of Maine works to make Maine a better and safer place to bike and walk. Founded in 1992, the Bicycle Coalition of Maine has grown into the leading bicycle and pedestrian advocacy group in the state.

Position Overview The Education Specialist plays a central role in advancing the Bicycle Coalition of Maine’s mission to make Maine a safer, more accessible place to bike and walk. This position leads and delivers high-quality bicycle and pedestrian safety education programming for youth and adults, with a primary geographic focus on southern...

Sea Bags are born as sails and transformed into nautically inspired totes and accessories that bring our customers great happiness. You see, we believe that sails soak up sun, salt, smiles and adventure.

Position Overview The ideal Assistant Manager for Sea Bags’ Flagship Store is a visible, hands-on leader who helps set the standard for team engagement, sales performance, customer experience, and brand presentation within a high-traffic, high-profile retail environment. Partnering closely with the Store Manager, this role drives results while developing team talent, maintaining...

$15-18/hour

WE CONNECT PEOPLE TO COMMUNITIES IN WESTERN MAINE THROUGH THE SUSTAINABLE MANAGEMENT OF HIGH QUALITY, DURABLE TRAILS AND WOODS FOR ALL SEASONS.

Position Overview Under the direction and supervision of the Trails Director, Lands Coordinator and Trail Crew Leader the Trail Crew performs trail maintenance and trail building tasks at a high quality, sustainable, and fun manner, sometimes in remote locations. The Trail Crew would typically work in concert with a 4–5-person team in...

$19-$22/hr

Our mission is to preserve and protect Harpswell’s natural resources, cultural heritage and access to the outdoors now and forever through conservation, stewardship and education. Essentially, we want to keep Harpswell a special place full of wonder and wildness, while also ensuring that people can access the outdoors for years to come!

Position Overview Are you someone that loves the outdoors, enjoys working with kids, and wants a meaningful summer job? Join our Nature Day Camp team and spend your days exploring forests, tide pools, and coastal trails while helping campers (ages 6–12) discover a lifelong connection to nature. This isn’t just a summer...

$11,500 living stipend

The Maine Island Trail is a 375-mile water trail for boaters that extends the length of the Maine coast. A recreational water trail, it connects over 250 wild islands and mainland sites that are open for day use or overnight camping.

Position Overview Island Caretaker (Two seasonal positions available) The Maine Island Trail Association (MITA) is a nonprofit organization working to promote environmental stewardship and responsible recreation on Maine’s coastal islands. MITA seeks two qualified island caretakers to help with the management and stewardship of two distinct State-owned islands in Casco Bay. One caretaker will...

OBP Trailworks, LLC provides design, construction and education services for all types of recreational trails. Since 2004, OBP has completed over 150 projects with international, federal, state, municipal, private and non profit organizations. Hallmarks of the company include community accessible trails, technical backcountry stone and timber craft, and trail system design projects.

Position Overview Position Description:  In addition to proficiently operating varied types of specialized trail machines, Equipment Operators are expected to have a diverse skill set and be willing to learn about many facets of trail maintenance and construction, both mechanized and hand built. Team members work approximately 40 hours a week. The...

$20+ hourly depending on qualifications and experience

Northeast Whitewater is a family oriented, nature based outdoor adventure destination that inspires vacationers, families and youth groups in outdoor educational pursuits, through guided interpretation in eco-tours, on water trips, whitewater rafting, wildlife and moose watching, at Northeast Whitewater Lodge, Campground & Guide Service at Moosehead Lake, Maine.

Position Overview Overseeing office, sales, and reservation operations, included responsibilities are: Work alongside and manage office and office staff, communicate and work alongside General Manager to ensure guest expectations are met. Social Media experience is preferred.  Answers guests inquiries in person, via phone and email and directs guests to appropriate activities, services...

$16-$18/hr

We are a daysail company based in Rockland, Maine, operating a 55′ wooden ketch. We offer 2-hour sailing tours, 6-hour island sailing/hiking trips and private charters for up to 21 guests on beautiful Penobscot Bay and the nearby islands.

Position Overview Description A Morning in Maine Sailing Tours is looking for ticket booth staff for a busy day charter business in Rockland.  We operate every day all season–mid-May to mid-October, weather permitting–running 2-4 trips per day depending on demand. Vessel is a 55’ LOA custom-built Pete Culler designed wooden ketch.  We...

$18-22 DOE

We are a daysail company based in Rockland, Maine, operating a 55′ wooden ketch. We offer 2-hour sailing tours, 6-hour island sailing/hiking trips and private charters for up to 21 guests on beautiful Penobscot Bay and the nearby islands.

Position Overview A Morning in Maine Sailing Tours is looking for deckhands for a busy day charter business in Rockland.  We operate every day all season–mid-May to mid-October, weather permitting–running 2-4 trips per day depending on demand. All summer sailing crew are expected to start in April for pre-launch maintenance and fit-out. ...

$7,700.00 - $8,000.00 per year

Girl Scouts of Maine builds girls of courage, confidence, and character, who make the world a better place. In Girl Scouts, girls of all backgrounds and abilities can be unapologetically themselves as they discover their strengths and rise to meet new challenges.

Position Overview Full job description Girl Scouts of Maine has an opening from late May to late August for a talented, dynamic Seasonal Camp Director for Camp Pondicherry in Bridgton, located in Maine’s beautiful Lakes Region. The Camp Director is a seasonal position responsible for managing all aspects of camp, including the...

Hourly pay based on experience

OBP Trailworks, LLC provides design, construction and education services for all types of recreational trails. Since 2004, OBP has completed over 150 projects with international, federal, state, municipal, private and non profit organizations. Hallmarks of the company include community accessible trails, technical backcountry stone and timber craft, and trail system design projects.

Position Overview Position Start Date:  April 27, 2026 - flexible Position End Date:   Nov. 20, 2026 - flexible Hiring Schedule:  Applications will be reviewed and interviews conducted on a rolling basis until all positions are filled. Position Description:  Professional Trail Crew Members and Leaders are expected to have a diverse skill set...

$450/week stipend

Northern Forest Canoe Trail is a 740-mile trail that follows historic waterways from Old Forge, New York, to Fort Kent, Maine.

Position Overview Six stewardship interns will work as teams to complete stewardship projects along the canoe trail. One three person team will work on projects from New York to Maine, and the other will be based in the Allagash Wilderness Waterway. Learn more.

4,500

The Chewonki Foundation is a non-profit institution in Wiscasset, Maine which runs educational programs with an environmental focus.

Position Overview Salary:$4,500.00 Annually Do you believe that the best classroom has no walls? Are you energized by paddling into the unknown, guiding young people through meaningful challenges, and building joyful community in wild places? Camp Chewonki is seeking Trip Leader & Adventure Staff to lead unforgettable backcountry expeditions and support dynamic adventure programming!...

Portland Paddle offers sea kayak and stand-up paddleboard (SUP) rentals, tours and lessons. We provide paddling adventures for all skill levels, including complete beginners. We’re located at the East End Beach a short drive or walk from downtown Portland. Our site on the waterfront of Casco Bay is perfectly situated for paddling.

Position Overview This position starts in April or May and extends through September. The Trips Manager’s (TM) performs crucial behind-the-scenes work that enables the rest of the staff to deliver outstanding paddling adventures to our customers. This role involves coordinating logistics, maintaining equipment, and ensuring effective communication among staff. The TM’s job...

$70,000 - $75,000/year

Hearty Roots is an esteem-building outdoor adventure program led by professional counselors & educators who also happen to be backcountry gurus.

Position Overview Build the Revenue and Voice Behind a Mission That Matters Hearty Roots is an award-winning, outdoor-based youth development organization advancing youth mental health through programs rooted in adventure, connection, and reflection. Guided by a credentialed team of professionals, our innovative, year-round programs served more than 1,000 Midcoast Maine kids and...

Makers of the finest canoes and kayaks. From fishing to recreation, we’ve been building watercraft since 1898. Find your next adventure at Old Town.

Position Overview Join our Team! At Johnson Outdoors, home to some of the world's most innovative and best-known outdoor recreation brands, we create amazing outdoor experiences- for adventurers, by adventurers. Old Town Watercraft brings over 100 years of passion and authentic understanding in kayaks, canoes and the new EPDL-power assist pedal kayaks...

Osprey’s Echo is a family-run sea kayaking company based in Stonington, on Deer Isle. Known for the archipelago of over 70 islands, Stonington offers a great deal for its visitors. Osprey’s Echo provide sea kayak tours into the archipelago and offerings range from 2-hour tours to 1/2 day, full-day and overnight camping trips. Osprey’s Echo have been in business since ...

Position Overview Reach out to kayak@ospreysecho.com for more info 🌲 Manage and maintain gear and kayaks at the waterfront 🌲 Greet guests and support customer service 🌲 May through September, with some flexibility on start or end dates 🌲 Looking for either full-time or part-time workers, but with flexibility to work occasional...

LifeFlight of Maine is the state’s only emergency air ambulance service. LifeFlight’s three helicopters, airplane, and specialty ground vehicles are equipped as fully functioning mobile intensive care units, bringing advanced skills, medical technology, pharmacy, blood, and more—directly to a patient’s side.

Position Overview This is an exciting opportunity for someone with nonprofit experience who wants to be part of a small and tight knit team, working for an organization that makes a tangible difference in lives, families, and communities across Maine. This person must have significant major/capital gift experience, be highly motivated, work...

HIOBS serves middle school, high school, gap year, and college students, as well as adults looking for wilderness adventure and Veterans from our Armed Forces.

Position Overview Logistics Coordinators are responsible for supporting the logistical and program functions of the regional program. This includes managing all logistical details, preparations, and support for courses in the field; coordinating the issue, de-issue, and maintenance of the regional outdoor equipment; helping to manage field and base food inventory, packing field...