Biking Overview
Overland offers biking trips for 5th through 12th graders in New England, in Canada's maritime provinces, along the Pacific Coast, across the U.S. and in Europe . We structure our trips to provide safe, fun and carefully crafted challenges that engage and excite our students. Our biking trips provide a life experience with value and resonance that extends far beyond the boundaries of a single summer.
For students currently in grade 5, we offer our Berkshire Adventure program. On this week-long trip, our students will be introduced to Overland's outdoor activities as they hike and bike in the beautiful Berkshires, climb Mt. Greylock and raft on the Deerfield River. An excellent introduction to outdoor adventure for our youngest students.
For students currently in grade 6, Overland offers our New England Adventure program. On this week-long trip, our students will be introduced to Overland’s outdoor activities as they bike on Martha's Vineyard, hike in the beautiful Berkshires and raft on the Deerfield River. For 6th graders looking for a two-week option, we offer our Mountains & Sea Adventure which includes hiking in New Hampshire, sea-kayaking Maine's rocky coast and bike rides on Nantucket Island.
For students currently in grades 7 through 9, we offer our classic two-week Cape Cod & the Islands bicycle tour. This trip offers quiet riding, beautiful beaches, fun coastal towns and a whale watch off Provincetown. Vermont, also open to students in grade 10, is a two-week trip that rides the length of Vermont through the rolling Champlain Valley and ends at the US/Canada border.
Students currently in grades 8 through 12 can choose from the following exciting bike trips. Nova Scotia & Acadia is three weeks of riding on country roads on Nova Scotia and in Acadia National Park, as well as sea-kayaking along Nova Scotia's spectacular coastline. Our Pacific Coast trip offers four weeks of biking from Seattle to San Francisco with a mid-trip break for white water rafting and a triumphant final ride across the Golden Gate Bridge.
For students in grades 9 through 12, we offer two bicycle tours in Europe and one across the United States. Paris to the Sea is a four-week trip across France, beginning in Paris, winding through the vineyards and châteaux of the Loire Valley and the hilltop villages of Provence to reach the Mediterranean. European Challenge is a four-week ride across Europe; starting in Amsterdam, The Netherlands riding through Belgium, Germany, Switzerland, France, and finally reaching Barcelona, Spain and the Mediterranean. The American Challenge is a six-week coast-to-coast test of determination and endurance, starting in Savannah, Georgia, and finishing some 3,000 miles west in Los Angeles, California.
Many of our biking itineraries have multiple sections that allow us to group students appropriately by age. For example, if there are two Nova Scotia & Acadia groups starting on the same date, one would typically be made up of students finishing 8th and 9th grades while the other would consist of students completing 10th through 12th grades.
If you need help choosing the right trip for you, please feel free to contact us or refer to the chart below.
| Trip Name | Difficulty | Difficulty Scale |
Description |
|---|---|---|---|
| Berkshire Adventure 1 week for 5th graders |
Easy | 1 | This program consists of day hikes, bike rides and rafting. |
| New England Adventure 1 week for 6th graders |
Easy | 1 | This program consists of day hikes, bike rides and rafting. |
| Mountains & Sea Adventure 2 weeks for 6th graders |
Moderate | 2 | This program consists of day hikes, bike rides and sea-kayaking. |
| Cape Cod & the Islands 2 weeks for grades 7-9 |
Moderate | 2 | Averages 20 miles on 10 riding days. Longest day ~38 miles. Total miles ~200. |
| Vermont 2 weeks for grades 7-10 |
Moderate | 3 | Averages 25 miles on 10 riding days. Longest day ~45 miles. Total miles ~250. |
| Nova Scotia & Acadia 3 weeks for grades 8-12 |
Moderate | 5 | Averages 35 miles on 15 riding days. Longest day ~55 miles. Total miles ~530. |
| Pacific Coast 4 weeks for grades 8-12 |
Moderate | 6 | Averages 45 miles on 22 riding days. Longest day ~70 miles. Total miles ~1000. |
| Paris to the Sea 4 weeks for grades 9-12 |
Moderate | 6 | Averages 43 miles on 21 riding days. Longest day ~75 miles. Total miles ~900. |
| European Challenge 4 weeks for grades 9-12 |
Challenge | 9 | Averages 70 miles on 20 riding days. Longest day ~85 miles. Total miles ~1,400. |
| American Challenge 6 weeks for grades 9-12 |
Challenge | 10 | Averages 82 miles on 38 riding days. Longest day ~125 miles. Total miles ~3,100. |


