Facebook Instagram Youtube
Find a Trek
Teen Treks - Bike Trips

Speak with a Bike Tour Guide: 1-716-566-7908

Cape Cod Bike Tour

Starts: Boston, MA

Route: Cape Cod

Starts: Boston, MA

Cape Cod Bike Tour

  • 2,995
  • 10 Days
  • 20-35 Miles per Day
  • Grade 9-11
  • Easy

Tour 1: June 28 – July 7
Tour 2: July 5 – July 14

 

Teen Tour: Bikepacking from Boston to Provincetown

Experience the quintessential New England summer on this 10-day cycling journey through Cape Cod and Martha’s Vineyard. From historic landmarks to sandy beaches, this trek offers a perfect blend of cultural exploration, natural beauty, and cycling adventure. Enjoy ferry rides, island camping, and plenty of stops for ice cream along the route.​
View 4 Dates
Learn More

Teen Tour: Bikepacking from Boston to Provincetown

Experience the quintessential New England summer on this 10-day cycling journey through Cape Cod and Martha’s Vineyard. From historic landmarks to sandy beaches, this trek offers a perfect blend of cultural exploration, natural beauty, and cycling adventure. Enjoy ferry rides, island camping, and plenty of stops for ice cream along the route.​
cape cod bicycle tour map

Start Your Summer Bike Tour

Tour Highlights at a Glance

Cape Cod Rail Trail

Cycle along this scenic trail through charming towns and coastal landscapes.

Ferry to Martha’s Vineyard

Explore the island’s unique character and picturesque vistas.

Beach Days

Relax on pristine beaches and enjoy swimming in the Atlantic Ocean.

Island Camping

Experience the joy of camping under the stars on Martha’s Vineyard.

Who Is This Teen Travel Program For

High School Students

Eager to explore the outdoors and embrace new challenges.

Intermediate Cyclists

Comfortable with daily rides of 20–35 miles on gentle terrain.

Nature Enthusiasts

Interested in experiencing the unique blend of history and natural beauty in New England.

Team Players

Ready to build lasting friendships and work collaboratively in a group setting.
teen trekkers in cape cod
teenage bicyclists in cape cod
teen bike tourists on the shores of massachusetts

Daily Itinerary & Map

What You’ll Experience Each Day on This Teen Tour

Please Note: Full detailed itineraries are only available to cyclists and their parents/guardians.

the plymouth rock monument

Boston & Plymouth Rock

Depart from Boston and cycle past Plymouth Rock onto Cape Cod.

lighthouse in woods hole

Cape Cod, Part I

Ride along the Cape Cod Rail Trail, exploring coastal towns and enjoying beach stops.

homes in martha's vineyard

Martha's Vineyard

Take a ferry to Martha’s Vineyard, set up camp, and explore the island's attractions.

beach in chatham, ma

Cape Cod, Part II

Return to Cape Cod, visit local landmarks, and enjoy group activities.

provincetown, ma

Provincetown

Conclude the trek with a celebratory gathering before returning to Boston.

Cultural & Regional Highlights

  • Plymouth Rock:

    Visit the historic site where the Pilgrims first landed.

  • Martha’s Vineyard:

    Explore the island's charming towns, lighthouses, and beaches.

  • Cape Cod:

    Experience the region's natural beauty, from rolling dunes to scenic bike trails.

lobster on ice at a cape cod restaurant
boats on herring river

Questions?

We're Here to Help You

Contact Us

The Inclusive Value of Every Teen Treks Journey

At TeenTreks, we believe in transparent pricing with no hidden fees. Your payment covers all aspects of the journey, ensuring a hassle-free summer adventure. Additionally, as a not-for-profit organization, 100% of trip profits are reinvested into supporting youth outdoor programs.

– Cliff Madell, Founder

What’s Included In the Trek?

This experience combines the structure of traditional summer camps for teens with the freedom of a cross-country bikepacking journey.

  • Equipment: High quality group camping, cooking and safety gear.
  • Accommodations: Campsite fees and select hostel stays.
  • Meals: All 30 meals and daily snacks during the trek.
  • Support: Experienced trek leaders.
  • Activities: Admissions to national parks and scheduled excursions.
collage of a bicycle, teenagers eating lunch, and a camp site
teen bicyclist taking a selfie

Safety, Supervision & Peace of Mind

  • 20+ Years

    Zero Major Safety Incidents

  • Experienced, Trained Trek Leaders

    Every leader is CPR/First Aid certified, highly trained in road safety, and selected for their maturity, energy, and care for teens.

  • Daily Safety Checks

    Bikes are inspected daily, safety briefings are held each morning and bike-safety managers are assigned daily.

  • Small Group Sizes

    We keep our groups intentionally small for personalized attention and stronger supervision.

  • Detailed Itinerary Shared Privately

    The full, day-by-day itinerary is shared only with trekkers and their parents or guardians for safety and privacy.

  • Daily Check-Ins

    Trekkers report a daily blog of the day's highlights to be shared with families, leaders report to office daily, office staff are available for updates anytime.

Classic New England Experience for Teens

This teen tour captures the essence of a New England summer, combining coastal riding, ferry crossings, and island exploration into a journey that feels both relaxed and rewarding. From Boston to Provincetown, teens experience bikepacking in a way that blends movement with memorable destinations.

  • The route mixes dedicated bike paths and quiet coastal roads, creating a smooth and enjoyable ride that keeps teens engaged without overwhelming them.
  • Ferry travel to Martha’s Vineyard adds a sense of adventure and variety, breaking up the journey with a unique island experience.
  • Daily highlights—from beach stops to ice cream breaks—give this one of the most well-rounded summer trips for teens seeking both fun and exploration.

Cape Cod & Coastal Highlights

The route showcases some of the most iconic landscapes in the Northeast, where seaside towns, bike trails, and open coastline create a constantly changing backdrop. Each segment introduces a new side of the region’s character.

  • Riding along the Cape Cod Rail Trail allows teens to move through forests, towns, and coastal stretches without heavy traffic, making each day feel relaxed and scenic.
  • Martha’s Vineyard offers a distinct shift in pace, with quiet roads, classic architecture, and ocean views that feel removed from the mainland.
  • Stops in places like Plymouth and Provincetown add cultural depth, connecting the journey to the history and identity of New England.

 

From Boston to the Outer Cape

The progression of this teen travel program is designed to feel like a true journey, starting in a historic city and gradually moving toward the more remote and windswept edges of Cape Cod.

  • The trip begins near Boston, where teens quickly transition from city surroundings into coastal riding and open landscapes.
  • Midway through the route, the ferry to Martha’s Vineyard creates a natural reset, giving riders time to explore and recharge.
  • As the group reaches Provincetown, the terrain opens up into dunes and wide ocean views, marking a memorable finish to the experience.

Confidence and Life Skills

For many teens, this is the first time they have been away from home for several weeks and faced such a clear personal challenge. The combination of distance, responsibility, and support creates powerful opportunities for personal growth that go far beyond cycling. 

  • Teens learn to manage their own gear, clothing, and daily routines, from packing in the morning to setting up tents and helping prepare meals at night.
  • Riding in varied terrain teaches pacing, perseverance, and thoughtful decision-making. They learn when to push, when to fuel up, and when to ask for coaching or support from leaders.
  • Shared challenges - headwinds, hills, or early wake-ups - become inside jokes and stories that riders bring back to school, future applications, or gap-year planning.

Reassuring Parents and Guardians

While riders focus on the next hill or the next viewpoint, parents and guardians prioritize structure, supervision, and safety. Our Portland-to-San Francisco route is designed for high school students, with experienced leaders, clear communication systems, and thoughtful pacing that acknowledges both teen enthusiasm and real-world limits.

  • Leaders receive training in road safety, first aid, group dynamics, and youth mentorship, combining the professionalism of established travel companies with a mission-driven focus on teens.
  • Group sizes are intentionally kept small so leaders can ride with participants, coach bike-handling skills, and respond quickly to changing conditions on the road or at camp.
  • Families benefit from transparent pricing and detailed pre-trip guidance, making it easier to plan, pack appropriately, and understand what each day on the road is likely to feel like for their teen.

How much time is spent on Martha’s Vineyard?

Teens spend multiple days on Martha’s Vineyard, allowing time to explore the island, enjoy beach activities, and experience a different pace of travel compared to the mainland.

Is this considered a beginner or intermediate teen tour?

This tour is best suited for intermediate riders who are comfortable with daily distances of 20–35 miles and ready for a slightly more dynamic route.

What makes this different from other teen tours?

This experience combines coastal riding, island travel, and cultural exploration into one continuous journey, offering more variety than traditional single-location programs.

A Memorable Way to Experience Cape Cod

Traveling by bike through Cape Cod and Martha’s Vineyard allows teens to experience the region in a way that feels connected and complete. Each mile builds on the last, creating a journey that feels earned rather than observed.

Riders experience the gradual shift from mainland towns to island life and finally to the outer reaches of Cape Cod.

The combination of cycling, beaches, and exploration creates a balanced and engaging experience from start to finish.

By the end of the trip, teens leave with a strong sense of independence and the confidence that comes from completing a meaningful journey.

Book a Teen Treks Bike Trip in Cape Cod

Contact our friendly team today to learn more and reserve a place for your teen.

Book Your Teen's Trip Today

Pricing, Dates & Availability

Cost: $2,995 / person

For 10 Days

Other bike tours charge the same price for just 6 days. Teen Treks gives you 10 days of adventure, learning, and lifelong memories – over 3x the value!

  • Early booking is recommended to secure your place.
  • 10 Days
  • 275+ miles
  • 30 Meals
  • 6 hostel/hotel overnights
  • 1:5 leader to trekker ratio
  • 10+ swimming opportunities
  • Countless ice cream stops
  • Tour Dates:
  • June 28 - July 7
  • July 5 - July 14
  • July 19 - July 28
  • July 26 - August 4
Alex
Trekker

"Cycling through Cape Cod and Martha’s Vineyard was an unforgettable experience. The landscapes were breathtaking, and the friendships I made will last a lifetime."

★ ★ ★ ★ ★

Your Leader

Get To Know Our Leaders

At Teen Treks, our bike trip leaders are passionate, experienced individuals who are committed to providing a safe and enriching experience for every teen. With backgrounds in outdoor education, cycling, and youth mentorship, they’re more than just guides—they’re mentors who foster teamwork, resilience, and personal growth. Through careful training in safety, first aid, and group dynamics, our leaders ensure every trip is both fun and supportive. They inspire teens to challenge themselves, build new friendships, and develop a lifelong love for adventure, making each bike tour a unique and unforgettable journey.

Learn More
teen bike tour photo on a giant chair
Cape Cod Trek

Dates & Pricing for Cape Cod Trek

Book now before we sell out. Start by clicking on your preferred date for more info and to reserve your trip.

$630.00 deposit $2,995.00 / person
Open
Filling Fast
Sold Out
$630.00 deposit $2,995.00 / person
Open
Filling Fast
Sold Out
$630.00 deposit $2,995.00 / person
Open
Filling Fast
Sold Out
$630.00 deposit $2,995.00 / person
Open
Filling Fast
Sold Out

Save Your Spot

We'll hold your spot for 3 days. No payment due now.

Tour Specific FAQs

Frequently Asked Questions About This Tour

What Makes the Cape Cod Bike Tour So Unique for Teens?

This teen tour combines coastal riding with ferry travel and island exploration, creating a bikepacking experience that feels varied and memorable from start to finish. Teens don’t just ride—they transition from Boston to Cape Cod and then to Martha’s Vineyard, each with its own pace and character. It’s one of the most well-rounded summer trips for teens, blending movement, scenery, and destination-driven experiences.

How Physically Demanding Is This Bike Trip?

This trip is best suited for intermediate riders, with daily distances of 20–35 miles on mostly gentle terrain. The mix of bike paths like the Cape Cod Rail Trail and quiet coastal roads keeps the riding manageable but engaging. Teens are challenged enough to grow, without feeling pushed beyond their limits.

What Types of Landscapes Do Teens Ride Through?

Riders experience a mix of forested bike trails, seaside towns, sandy beaches, and open coastal stretches. The route includes iconic New England settings like Cape Cod dunes and the unique island environment of Martha’s Vineyard. Each day offers a different backdrop, from shaded paths to expansive ocean views.

How Do Teens Handle Being Away From Home for So Long?

The 10-day structure provides a balance between independence and support, making it manageable for teens. Small group dynamics and consistent daily routines help teens settle in quickly. Shared experiences—like camping, meals, and beach time—create a strong sense of connection and comfort.

What Happens on Rest Days or in Major Cities?

Time off the bike is built into the journey through beach days, island exploration, and time in towns like Provincetown. On Martha’s Vineyard, teens spend multiple days exploring, relaxing, and enjoying activities beyond cycling. These moments give riders a chance to recharge while still staying engaged in the experience.

Is This Trip Safe for Teens Over Such a Long Distance?

Safety is built into every part of the experience, from trained leaders to daily bike inspections and structured riding plans. Routes are chosen for their bike-friendly conditions, including dedicated paths and low-traffic roads. Small group sizes allow leaders to stay closely connected to each teen throughout the tour.

Who Is the Ideal Fit for the Cape Cod Bike Tour?

This teen tour is ideal for high school students with some cycling experience who are ready for a more dynamic route. It’s a strong fit for teens who enjoy the outdoors, coastal environments, and exploring new places with a group. The combination of riding and destination experiences appeals to a wide range of interests.

How Should Teens Prepare Physically for a Longer Trip?

Teens should be comfortable riding moderate distances before the trip begins. A few weeks of regular riding, along with general fitness activities, will help build confidence. The structure of the program supports gradual improvement, so teens grow stronger and more capable as the journey unfolds.

General Tour FAQs

More About Our Teen Travel Program

Where do we sleep?

Teen Treks groups stay in hostels, hotels, and campgrounds. Wherever you go, you’ll get to know the place. In a major city, you’ll likely get to stay in a hostel right in the downtown area, steps from major tourist attractions and plenty of great restaurants. In the North American or European countryside, you’ll often camp out in beautiful settings, or stay in a hostel that’s part of a historic landmark. Our Lake Ontario Trek, for example, stays at the 1800s-era Tibbets Point Lighthouse hostel.

What are the trip leaders like?

Each group gets two leaders, who will be fun, resourceful adults who love hanging out with kids and who know bikes. Many took cross-country bike trips as teenagers like the ones they’re now leading, and they all complete a comprehensive leader training program and get CPR and First Aid certification. They’re teachers, human service professionals, travel and hospitality professionals, graduate students and college seniors. Some are avid cyclists and travel enthusiasts, while others have served in organizations like Americorps. Their average age is 25 years old.

What makes Teen Treks different?

Teen Treks gives teenagers the chance to discover the excitement and fun of bike touring with a bunch of like-minded people, seeing beautiful natural landscapes and world-class cities while gaining independence and travel skills. You’ll have great experiences out on the road and make memories that will last a lifetime.

Teens who take our trips get a lot of say in what the group does each day, from planning the details of the route to picking out what’s for dinner. If everyone wants to bike hard and get to the beach faster, you can do that. If you want to spend a little more time taking pictures at a breathtaking waterfall or a picturesque waterfront, you can do that. We give our trip leaders lists of activities and interesting sites along the route, but the group has the freedom to follow their preferences – every summer, our trekkers find things to do we didn’t know about, and we add them to our lists for next year.

Teen Treks offers by far the best value in truly extraordinary bike trips for teenagers. Over our history, we’ve run outstanding trips up and down the New England Shore from New York to Montreal, in the Pacific Northwest, and along the California Coast all the way Across America, and through the best sites in Europe. Check out our testimonials and compare our prices to other organizations’. Our trips, our experience, and our rates can’t be beat.

What do we eat?

Your leaders will make sure there’s plenty of food for everyone, and that it’s tasty as well as good for you. Breakfast will be quick but satisfying – hot oatmeal or cereal, for example – and lunch will keep you going with a variety of fruits, vegetables, and sandwiches. For dinner, you may go to a local restaurant or make something hot together, like pasta, flatbread pizzas, or fajitas.

Our trips readily accommodate those with special dietary requirements, and we’re very conscious of food allergies – just let us know what you need.

What kind of bike should I bring?

We recommend using a touring bike, a road bike, or a hybrid with at least 15 speeds; 15-27 is ideal. If you need to buy a bike, you should be able to get one that will work great for touring for $400-$1000. Teen Treks does not allow participants to use high-performance racing bikes, dirt bikes, fixed-gear bikes, or Dutch-style roadsters.

Your bike should have a set of new tires at the time your trip starts.

Please call or email us if you’d like to talk bike choices.

Who goes on a typical Teen Trek?

Our groups include up to 10 teens, led by 2 outstanding leaders. We try to keep the gender balance even, half boys and half girls, and we group teens by age to create a positive, cohesive social environment.

Some of our trips, like the European Phantom and Pacific Northwest Treks, are designed for older teens, where others, like the Niagara-Toronto trek, cater to a younger age group. When a route will work well for kids across a range of ages, we run several trips, one for each age group. Check out our Trips Table to see what trips we have for your age.

Teens who travel with us have come from all 50 states, Canada, Europe and Asia.

How will I keep in touch with home?

You’ll be able to call home for short chats using the leader’s cell phones every 6-7 days. We provide parents with a trip itinerary and we post regular updates on our blog to show off the adventures our trekkers are having. In addition, leaders touch base with the Teen Treks office daily, so parents can contact us for information as the trip progresses.

What happens on rainy days?

If it’s only raining lightly, the trip will carry on as planned. Heavy rains or thunderstorms are usually short-lived, so your group will sit out the storm in a coffee shop, at a store, or in some other sheltered location, and continue on your way once it passes.

Cape Cod Bike Tour is now open for booking.
View Dates