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Teen Treks - Bike Trips

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New England Shore Bike Tour

Starts: New York City, NY

Route: New England Shoreline

Ends: New York City, NY 

New England Shore Bike Tour

  • 4,495
  • 16 Days
  • 20-35 Miles per Day
  • Grade 9-12
  • Easy

Tour 1: June 28 – July 13
Tour 2: July 5 – July 20

 

Teen Tour: Bikepacking from New York City to Boston

Kick off a 16-day journey along the scenic coastlines of New York, Connecticut, Rhode Island, and Massachusetts. From the bustling streets of New York City to the historic charm of Boston, this trek offers a perfect blend of coastal beauty, cultural exploration, and cycling adventure. Experience the rich maritime heritage of New England, relax on pristine beaches, and immerse yourself in the vibrant communities along the way.
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Teen Tour: Bikepacking from New York City to Boston

Kick off a 16-day journey along the scenic coastlines of New York, Connecticut, Rhode Island, and Massachusetts. From the bustling streets of New York City to the historic charm of Boston, this trek offers a perfect blend of coastal beauty, cultural exploration, and cycling adventure. Experience the rich maritime heritage of New England, relax on pristine beaches, and immerse yourself in the vibrant communities along the way.
new england shores bike tour map

Start Your Summer Bike Tour

Tour Highlights at a Glance

Coastal Exploration

Cycle through picturesque towns like Mystic, Newport, and Providence.

Block Island

Spend two days exploring this cyclist-friendly paradise.

Rhode Island Beaches

Relax on white sandy shores and enjoy the ocean breeze.

East Bay Bike Path

Ride along this scenic trail offering stunning waterfront views.

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.

Culture Enthusiasts

Interested in experiencing the unique blend of history landscapes modernity in New England.

Team Players

Ready to build lasting friendships and work collaboratively in a group setting.
teen trekkers in cape cod
teen bike tourists in cape cod
bike tourists on connecticut beach

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.

Five Mile Lighthouse in New Haven CT

New York & New Haven

Depart from New York City and cycle through scenic shoreline towns like Norwalk and New Haven.

mystic seaport

Mystic

Visit maritime gems like Stonington & Groton. Cross into Rhode Island to relax on Narragansett’s beaches.

North Lighthouse, Block Island, Rhode island

New Shoreham

Ferry to Block Island for unforgettable days cycling around cliffs, beaches, and rolling meadows—no cars.

Breakers and Cliff Walk - Newport, Rhode Island

Newport

Ride through Newport’s mansion-lined avenues and follow the East Bay Bike Path into Providence.

artist chanties in cape cod, massachusetts

Cape Cod & Boston

Cycle scenic backroads to reach the Cape. Explore Freedom Trail landmarks and enter the city of Boston.

watermill in sandwich massachusetts

South New England

Begin your journey back south. Cycle through peaceful towns with classic New England charm.

new york city towers world trade center

The Big Apple

Conclude your adventure with a celebratory return to New York City.  Enjoy the nightlife with new friends.

Cultural & Regional Highlights

  • Providence:

    Experience the vibrant arts scene and diverse culinary offerings.

  • Cape Cod:

    Enjoy the region's natural beauty, from rolling beaches to charming villages.

  • Boston:

    Explore landmarks like the Freedom Trail and indulge in the city's rich history.​

fried clams in cape cod
A view from a boat towards Bowens Wharf at Newport

Questions?

We're Here to Help You

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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.
  • Accomodations: Campsite fees and select hostel stays.
  • Meals: All 48 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.

A Coastal Teen Tour Built for Exploration

This teen tour follows the rhythm of the coastline, where each day brings a new town, a new view, and a new stretch of road shaped by the Atlantic. From city streets to quiet shoreline paths, the experience feels constantly in motion without ever feeling rushed.

  • Riders move through a mix of vibrant coastal towns and peaceful backroads, creating a balance between energy and reflection.
  • The proximity to the ocean keeps the journey fresh, with sea air, open views, and frequent beach access shaping the experience.
  • As one of the more immersive summer trips for teens, the route offers a strong sense of progression across multiple states and regions.

New England’s Highlights

This section of the country is defined by its maritime history, walkable towns, and scenic waterfronts. Each stop along the route offers a slightly different perspective on New England life.

  • Teens ride through well-known coastal destinations like Mystic, Newport, and Providence, each with its own character and pace.
  • Block Island stands out as a highlight, offering quiet roads, ocean cliffs, and a rare chance to cycle in a car-free setting.
  • The East Bay Bike Path provides one of the most scenic stretches of the trip, with uninterrupted views along Narragansett Bay.

NYC to Boston and Back Again

This teen travel program is structured as a true journey, beginning in New York City and expanding outward before returning with a completely different perspective.

  • The early days focus on leaving the density of New York behind, transitioning into Connecticut’s shoreline and smaller coastal communities.
  • Midway through the trip, the experience opens up with ferry crossings, island riding, and time spent in Rhode Island’s beach towns.
  • The approach into Boston delivers a milestone moment, followed by a return south that allows teens to reflect on how far they’ve come.

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 do teens spend biking versus exploring?

Each day blends riding with time off the bike. Teens regularly stop in towns, visit beaches, and explore destinations like Newport and Boston.

Is this considered one of the more immersive teen tours?

Yes, the length and variety of this route make it one of the more immersive teen tours, offering a deeper experience than shorter, single-location trips.

What makes Block Island a highlight of this trip?

Block Island offers a rare combination of quiet roads, ocean views, and a relaxed pace, giving teens a break from structured riding while still staying active.

A Different Way to Experience the Coast

Seeing New England by bike changes how the region feels. Instead of passing through quickly, teens experience the coastline as a connected journey shaped by distance, effort, and discovery.

Riders notice the subtle shifts between regions—from Connecticut’s shoreline to Rhode Island’s beaches and Massachusetts’ historic towns.

The combination of cycling, ferry travel, and coastal exploration creates a layered experience that feels both active and memorable.

By the end, teens leave with a stronger sense of independence and a clearer understanding of what it means to complete a real journey.

Book a Teen Treks Bike Trip in New England

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: $4,395 / person

For 16 Days

Other bike tours charge the same price for just 6 days. Teen Treks gives you 16 days of adventure, learning, and lifelong memories – over 3x the value!

  • Early booking is recommended to secure your place.
  • 16 Days
  • 450+ miles
  • 48 Meals
  • 6 hostel/hotel overnights
  • 1:5 leader to trekker ratio
  • 10+ swimming opportunities
  • Countless ice cream stops
  • Tour Dates:
  • June 28 - July 13
  • July 5 - July 20
  • July 19 - August 3
  • July 26 - August 10
Emily
Trek Leader​

"I was a Teen Trekker myself and did the New England Shore Trek and I had an amazing time. I can't wait to create more memories."

★ ★ ★ ★ ★

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
New England Shore Trek

Dates & Pricing for New England Shore Trek

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Tour Specific FAQs

Frequently Asked Questions About This Tour

What Makes the New England Shore Bike Tour So Unique for Teens?

This teen tour connects multiple iconic coastal regions into one continuous bikepacking journey, from New York City to Boston and back. Teens don’t just visit destinations—they ride between them, experiencing the coastline as it unfolds through towns like Mystic, Newport, and Providence. The addition of Block Island, with its car-free roads and ocean cliffs, creates a standout experience you won’t find in most teen travel programs.

How Physically Demanding Is This Bike Trip?

Daily rides typically range from 20–35 miles on gentle terrain, making this manageable for intermediate riders. The route includes bike paths like the East Bay Bike Path and quiet shoreline roads, which reduce stress and allow teens to focus on the experience. Over 16 days, the challenge comes more from consistency than steep climbs.

What Types of Landscapes Do Teens Ride Through?

Riders experience a mix of coastal roads, beach towns, and scenic bike paths that hug the Atlantic shoreline. The terrain shifts from Connecticut’s historic harbors to Rhode Island’s sandy beaches and Massachusetts’ coastal villages. Highlights like Block Island and Narragansett Bay bring open ocean views, rolling terrain, and a strong sense of place.

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

The structure of this teen travel program helps teens quickly adapt to life on the road. Shared routines—riding, eating, and camping together—create a strong group dynamic that replaces homesickness with connection. As the days progress, teens gain confidence and begin to feel fully comfortable in the rhythm of the journey.

What Happens on Rest Days or in Major Cities?

This trip blends riding with meaningful time off the bike, especially in places like Newport and Boston. Teens explore landmarks like the Freedom Trail, walk waterfront areas, and experience local culture in each city. Time on Block Island also offers a more relaxed pace, giving riders space to recharge while still staying active.

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

Safety is built into every part of this teen tour, from experienced leaders to carefully selected routes. Daily safety checks, small group sizes, and bike-friendly paths reduce risk and allow for close supervision. Parents can feel confident knowing the trip is structured, monitored, and supported from start to finish.

Who Is the Ideal Fit for the New England Shore Bike Tour?

This trip is best suited for high school students who are comfortable with moderate daily rides and excited to explore new environments. It’s a great fit for teens who enjoy a mix of nature, beach time, and city exploration. Those who thrive in group settings and want a more immersive travel for teens experience will get the most out of it.

How Should Teens Prepare Physically for a Longer Trip?

Building comfort with consecutive days of riding is the most important step before this trip. Regular biking, even on flat terrain, helps develop endurance for a multi-day journey. Teens don’t need to be elite athletes—the program is designed to build strength and confidence as the trip progresses.

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.

New England Shore Bike Tour is now open for booking.
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