Overland welcomes our youngest students to join us for a week of exploration in the beautiful Berkshires, as we hike hills and mountains, cycle a quiet bike path and raft an exciting river on Berkshire Adventure.
Few settings could equal the Berkshires and the southern Green Mountains as locations for an introductory Overland program. Gentle hills become mountains and clear rivers flow past old farms and postcard-perfect New England towns. With a wide range of fun outdoor activities—from hiking, biking and rafting to camping and playing games—the Berkshires and the Green Mountains are perfect for our weeklong program. We’ll begin with easier hikes and walks, building up to our hike of Mount Greylock, the highest point in Massachusetts. We’ll also spend a day cycling the countryside on the beautiful Ashuwillticook Rail Trail and enjoy a day of rafting on the Deerfield River.
At trip’s end, we’ll celebrate all that we have accomplished and seen on Berkshire Adventure—the perfect introduction to Overland.
“Everyone helped make Nicholas’ first time away from home a happy, memorable, growth experience.” Amy Van Buren, Fairfield, Connecticut
From Lake Sunapee in New Hampshire to South Beach on Martha’s Vineyard, Mountains & Sea Adventure offers two weeks of exploration and fun as we hike, bike, raft and kayak New England’s mountains and coast.
The pristine water of Lake Sunapee, the expansive views of Mount Monadnock and the quiet bike paths of Martha’s Vineyard provide beautiful settings for our introductory program. Our trip begins with a short afternoon hike to stretch our legs and get to know each other. Then we’ll travel to New Hampshire’s beautiful Lake Sunapee region for hiking, swimming and camping. Our challenge hike up Mount Monadnock will allow a rewarding six-state view from the summit. Then we'll head down to Martha's Vineyard where we'll bike on the bike paths and quiet back roads of the island, visit bustling Vineyard Haven and classic Edgartown, and enjoy picnic lunches and afternoons at the beach. Our final activity on Martha's Vineyard will be an afternoon exploring the picturesque coastline by sea kayak.
At trip’s end, we’ll enjoy a day of rafting on the Deerfield River, and then return to Williamstown to look back on all of our achievements on Mountains & Sea Adventure.
"My daughter came home a year older! She’s more confident and independent for the experience." Karen Saklad, Maple Grove, Minnesota
Join us for a week of hiking, swimming, biking and rafting as we explore the best of New England on New England Adventure.
We’ll start in Williamstown, Massachusetts, with a short orientation to get to know each other before we travel by van to southern Vermont. While enjoying quintessential New England—white-steepled churches, red covered bridges, quaint villages, fields and farms—we’ll bike in Franconia Notch State Park and enjoy day hikes with our group. In Hanover, New Hampshire, we’ll hike along the famous Appalachian Trail. We’ll hike a 4,000-foot peak in New Hampshire's White Mountains, and raft the exciting Deerfield River. In the evenings, we’ll play games, build campfires and make s’mores.
At trip’s end, we’ll celebrate all that we have accomplished and seen on New England Adventure.
“I had the best leaders you could ask for. Thank you for the amazing experiences and challenges." Zach Buccellato, Skillman, New Jersey
North Country Adventure offers two fun weeks of hiking, biking, kayaking and rafting in New York’s Adirondacks and Vermont’s Green Mountains.
Soon after meeting up in Williamstown, Massachusetts, we’ll head to picturesque Arlington, Vermont, for day hikes and bike rides. We’ll also enjoy time on the water as we kayak the peaceful Battenkill River. Next, we’ll travel west to camp along the shores of beautiful Lake George. We’ll raft the exciting Hudson River Gorge and summit Cascade Mountain, one of the famous Adirondack High Peaks. Returning to Vermont, we’ll bike along Lake Champlain and visit bustling Burlington. Our final hike will take us along the famed Long Trail to the top of Camel’s Hump, where we’ll have spectacular views from the summit.
At trip’s end, we’ll return to Williamstown and celebrate the friendships, fun and accomplishments of North Country Adventure.
"I cannot pick one favorite part of the trip; everything was amazing." Luke Pailet, Concord, Massachusetts
Overland’s Sierra Adventure offers the opportunity to explore California’s high country at its finest. For two weeks, we’ll hike the Sierras, raft the exciting American River and kayak scenic Lake Tahoe, the largest alpine lake in North America.
We’ll gather in San Francisco before heading east to Lake Tahoe, where we’ll swim in Tahoe’s brilliant blue water, kayak pristine Emerald Bay and hike high above the lake. We’ll then drive south to tackle more challenging hikes in the wildflower-filled valleys and granite peaks of Stanislaus National Forest. We’ll wrap up our time in the Sierras with a day of rafting on the American River—a great way to finish a fantastic two weeks in California.
For our last night, we’ll return to San Francisco to celebrate all of our accomplishments in the rugged and beautiful California mountains.
“Sierra Adventure was fantastic. The leaders made such a difference—both were amazing. Julia will definitely return next summer.” Suzanne Fox, Falmouth, Maine
In Yellowstone and Grand Teton National Parks, we’ll hike rugged mountains, kayak on Yellowstone Lake and raft the Snake River, as we spend two weeks exploring these world-famous parks.
At the start of our trip, we’ll explore the Tetons with a naturalist who will teach us about the plants and animals found in this beautiful setting. We’ll then head north into Yellowstone National Park and hike with day packs, taking frequent breaks to enjoy the big views of the Yellowstone backcountry. We’ll spend a day kayaking with guides on Yellowstone Lake where we’ll see wildlife from the water, kayak near thermal features and learn basic paddle strokes. During our trip, we’ll take time to see Old Faithful, as well as the Grand Canyon of Yellowstone. We’ll also raft the Snake River—a perfect choice for beginners.
At the end of the trip, we’ll head back to Jackson for our last night to celebrate all of our adventures out West.
“My leaders made my first camping experience so much fun. Thank you!” Audrey Berner, Dallas, Texas
This classic tour of Cape Cod, Nantucket and Martha’s Vineyard is always one of Overland’s most popular trips—and for good reason. Daily rides explore beautiful beaches and picturesque towns on back roads and bike paths. Cape Cod & the Islands offers challenge, camaraderie, biking, beaches and whale watching off Provincetown.
We’ll start in Williamstown, Massachusetts, with a short orientation and a practice ride before we travel by van to Cape Cod. On the Cape, quiet back roads and beautiful beaches await us. We’ll ride through Hyannis, Brewster and Wellfleet on bike paths and scenic roads that take us through forests, by marshes and past beaches. The terrain is forgiving, allowing us to build skills and fitness as we go. In Truro, we’ll face some challenging hills as we bike through an area of big sand dunes with beautiful views of Cape Cod Bay to the west and the Atlantic Ocean to the east. On Nantucket and Martha’s Vineyard, bike paths take us to classic seaports, charming towns and long stretches of white sand—perfect for an afternoon of swimming and games.
Our daily rides average 20 miles and are a great way to discover the beauty of the Cape and the islands while making friends and having fun on a summer adventure. A whale watch off Provincetown rounds out two weeks of biking, beaches and fun on Cape Cod & the Islands.
“Sarah learned to be more self-reliant and work with a group. She also came back feeling a great sense of accomplishment! She loved it!" Resa Petrick, Brooklyn, New York
Famous for its beautiful vistas, quiet roads and small, friendly towns, it’s no secret that Vermont is a perfect setting for bicycle touring. Our daily rides over rolling terrain offer stunning views of Vermont’s Green Mountains, Lake Champlain and New York’s Adirondacks.
We’ll begin in Williamstown, Massachusetts, with an orientation and short practice ride that focuses on safe riding. We’ll then load our bicycles and begin our trek to the Canadian border. On daily rides that average 25 miles, we’ll bike along green fields, through covered bridges, by red barns and past white-steepled churches. We’ll ride through the Lake Champlain Valley, seeking out quiet roads and gentle grades. As we head north, we’ll bike along stunning Lake Champlain and look west to the imposing Adirondacks. To the east are Vermont’s Green Mountains with impressive Mount Mansfield, Vermont’s highest peak, in the distance. We’ll take a day to visit Burlington, a nice contrast to the small towns and big farms along our route. Each day brings fun and discovery and, at day’s end, comfortable camping awaits us.
Near the end of our journey, we’ll ride triumphantly to the Canadian border. After reaching our goal, we’ll return to Williamstown by van to celebrate the accomplishments and fun of our two weeks together.
"My favorite part of the trip was the biking. The scenery was beautiful, and the pace at which we rode was perfect." Jason Landes, Framingham, Massachusetts
Ride from Boston to Bar Harbor and along the rocky coast of Acadia National Park on this three-week exploration of New England’s famous coast.
We’ll meet our group at Boston’s Logan Airport and take a short van ride to our first campsite on the North Shore. From there, on daily rides that average 30 miles, we’ll work our way north, cycling through Massachusetts, along New Hampshire’s seacoast and into southern Maine on our way towards Portland and Freeport. We’ll then take a break from the bikes to enjoy two days of sea kayaking on the picturesque Maine coast.
From Freeport to Bar Harbor, our ride shows us the best of Maine: quaint small towns, busy harbors filled with lobster boats, quiet coves and rocky islands. Each day brings fun and exploration and, at day’s end, comfortable camping in state parks and private campgrounds awaits us. Our route finishes in Acadia National Park, where we’ll cycle to the top of Cadillac Mountain to celebrate our ride along the New England coast.
At trip’s end, we’ll drive to Portland, Maine, to enjoy a dinner out as we look back on three weeks of beautiful riding, great friendships and lots of fun on New England Coast.
"Brian can't wait to do another Overland ride next summer!" Melanie Rose, Paradise Valley, Arizona
Canada’s maritime province of Nova Scotia offers picturesque shorelines, charming harbors and friendly people. Maine’s Acadia boasts similar delights: waves crashing into rocky coves, lobster boats in morning mist, gulls overhead and seals in the distance. Come explore these extraordinary destinations by bicycle on Nova Scotia & Acadia.
We’ll meet in Portland, Maine, and make our way by van and ferry to Nova Scotia where our ride begins. In Nova Scotia, we’ll bicycle quiet country roads over rolling hills, through small towns and past sandy beaches. Averaging 35 miles a day, we’ll ride to Kejimkujik National Park, where we’ll explore the park and beautiful Kejimkujik Lake. In Lunenburg, we’ll take a break to sea kayak the island-dotted coast. Our ride then takes us to southern Nova Scotia and the famous Lighthouse Route. We’ll make our way back to the Bay of Fundy and ferry across the water. We’ll spend our last few days in beautiful Acadia National Park. There, our challenge ride will take us to the summit of Cadillac Mountain—a fitting high point for our three weeks of riding.
At trip’s end, we’ll return to Portland to celebrate our accomplishments and our time together.
“My first Overland experience was amazing thanks to my leaders and my wonderful Overland family.” Rhianna Patel, Sudbury, Massachusetts