Private Lessons

Private or Semi-Private lessons is a program-offering we’ve wanted to grow for the past few years, but it never took priority because we all love and value the group experience so much. But now with Covid-19 restrictions, it’s a great way for us to continue our mission and provide access to the outdoors in a more private setting! We believe in the power of the outdoors and know that adventure can bring about healthy change in people’s mental and physical lives. We hope you’ll consider signing up for a Private Lesson with one of our staff or Per Diem trip leaders and participate (with guidelines) in an outdoor excursion that helps you get exercise, fresh air, and a mental-health boost!

Lessons are between 1.5 Hours and 3 Hours and you and your Waypoint Instructor will determine, together, best fit on location and activity type. Whether you’re signing up for a Private Lesson or just going out on an adventure on your own, Waypoint recommends following these guidelines. Please review these before you join us.

Choose one of the following options for a private or semi-private lesson.

Option #1: ADVENTURE WITH A WAYPOINT STAFF MEMBER: Utilize the expertise of our experienced team and get access to the locations and equipment that would best suit your goals and needs. Our team has years of experience and we are constantly evaluating and re-evaluating best sites, trails, boat launches, and equipment to best suit your needs. Please note, bathrooms may not be available at all locations. If a bathroom is a “must-have”, let us know and we will do our best to find a location where there is one or look into best portable bathroom options for you. Email Julia to sign up! Include your activity of choice and what town you’d be coming from.

– Hiking (Private) – *$100 Specialized equipment, instruction, skill-building, and personalized instruction all included. A third person from your home must be present (see below in More Details for “third person” guidelines). Someone from our team will determine with you a date, time, and place that works best and design an experience that meets your needs and goals.

– Hiking (Semi-Private) – *$150 – a Semi-Private Hike would be for two or more participants coming from separate households to socially-distant hike together. This could be a great break for parents and/or a great way to reconnect with friends while doing something fun. Specialized equipment, instruction, skill-building, and personalized instruction all included.

– Kayaking (Private or Semi-Private) – *$150 – Enjoy the peace and serenity of the water on a kayaking adventure! Check eligibility criteria in Covid-19 Confirmation form for more details. At this time, participants must be able to either paddle independently in their own single kayak or have someone from their household join in a tandem kayak who is a competent paddler. Some exceptions may apply. Please reach out if you have questions.

– Cycling or Biking (Private or Semi-Private) – *$150 – Get out on a sidewalk or trail and feel the speed! We have tandem road-bikes to provide (if you have someone from your household who is a competent tandem-bike peddler to ride with you), but otherwise you bring your own bike. We can go road-biking on paved paths and sidewalks or go trail biking with mountain bikes on the trails!

*Prices above reflect typical year-round fees for Private Lessons and what it costs to run these individual excursions. Please note: it is our first and foremost priority to provide these to you regardless of what you can pay. Please reach out to sign up even if price is a barrier. We will determine a price or lack-there-of that you are comfortable with. In addition, donations in any amount help fund this opportunity for others. Payment and donations are discussed during your registration.

Option #2: I DON’T NEED MUCH SUPPORT. I JUST WANT TO GO FOR A WALK WITH A PER DIEM TRIP LEADER: We have a strong team of capable trip leaders with various schedules and areas of expertise. If you don’t need special equipment or the experience of a Waypoint staff member, a Per Diem Trip Leader may be a great match for you. The team is mostly comprised of hiking trip leaders, but kayaking and biking adventures are available upon request. Tell us a little more about yourself and we’ll play matchmaker with one or two of our trip leaders that will then make plans with you to meet up. All Essential Eligibility Criteria and policies below still apply. *Suggested donation of $50 to cover set-up fees. Email Julia to sign up. Include your activity of choice and what town you’d be coming from.

OPTION #3: I JUST WANT TO RENT EQUIPMENT: If you don’t need the support of a Waypoint staff or Per Diem Trip Leader and just want to rent an off-road wheelchair, trekking poles, or adaptive paddling set-up, check out our Wheelchair Rental Program page which includes info on how to rent our adaptive recreation equipment.

More details about Private Lessons:

  1. Forms:  You will have to fill out both the Waypoint Adventure Medical Info form AND a Covid-19 Confirmation form. Please read these over carefully and especially consider if the Essential Eligibility Criteria on the Covid-19 Confirmation form applies to you before you sign.
  2. Third Person:  There will always be a “third party” present. We will work with you to determine who that third person may be. It’s one of our policies that staff and participants can’t be alone out of sight of the public at any time. We’ll ask you if you have a family member or person you’ve been isolating with who wants to join us. If you don’t, we can work on our end to recruit a volunteer to join us instead.
  3. Masks and Hand Sanitizer: We ask that you bring your own mask and hand sanitizer to your lesson. We’ll have extra if you forget. We’ll only require mask wearing when we are within 6ft of each other.
  4. Bathrooms:  Please be aware that many bathrooms are not in service. If there is not a bathroom at the location, we recommend using the bathroom at your home before you come and then if we need to use the bathroom in the woods, check out our How to Use the Bathroom in the Woods video on our YouTube channel. If a bathroom is a “must-have,” let us know and we will do our best to determine best options for you.
  5. Transportation:  You must provide your own transportation to and from these Private Lessons.
To sign up for private lessons, email Julia:

Include your activity of choice (hiking, kayaking, biking) and what town you’d be coming from.



Check out pictures of Private Lessons during our “Trial Phase”:


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