Top New England Bike Tours

Discover Boston’s top attractions on this comprehensive guided bike tour around the city. See the unique character and charm of each community up close, like the beautiful brownstones in Back Bay and the South End. Visit Boston’s historic North End and pedal past Copley Square and Fenway Park. Cross the Freedom Trail, passing significant locations to United States history.

Lighthouses are an iconic image associated with coastal Maine and Portland showcases some from the 1800s. Join this bicycling tour in Portland and see two of the city’s lighthouses from the 19th century. Follow quiet roads along South Portland’s coast to reach a small lighthouse called Bug Light, still in use today. Ride farther to Spring Point where a larger lighthouse awaits at the end of a long granite breakwater.

Explore the lighthouses of the South Portland Greenbelt Pathway by bicycle with this guided tour. You'll visit Bug Light, Point Ledge Light, and Portland Head Light with a local guide. You'll also have the chance to stop at a local food truck for a lunch of lobster rolls before returning to your starting point.

Discover the landscapes of New Hampshire's coast on a small-group bike tour traveling from island to island. Visit New Castle, see the Isle of Shoals, ride across the Piscataqua River, and get views of the Atlantic Ocean. Explore the best of Portsmouth and New Castle while stopping en route to hear some interesting history and storytelling. Cover more ground than you would on a walking tour with some hills, varied scenery, and dramatic views.

Discover the lighthouses and coastal landmarks of Portland on a small-group biking tour. Hop on a provided bicycle and follow your guide to the Bug Light, Spring Point Ledge, and Portland Head lighthouses. Along the way, learn about their storied histories. Other highlights include the Liberty Ship Memorial, Cape Elizabeth, and Willard Beach. Set at a leisurely pace, the adventure also includes a complimentary lobster roll lunch at an award-winning food truck.

Experience the charms of Cambridge on this bicycle tour. Sometimes referred to as “Boston’s Left Bank,” Cambridge is a celebrated hub for academia, technology, and culture. Ride across the gleaming waters of the Charles River and visit Harvard Square, MIT, the Stata Center designed by Frank Gehry, and more. Over the course of 2.5 to 3 hours, you’ll cover 11-13 miles in this bike-friendly area.

Explore the Portland Peninsula by bike with this small-group guided tour. Start at the Eastern Promenade, making your way along the waterfront bike path until you reach the Back Cove Trail. Your guide takes you to the Old Port to see some of the City of Portland's prettiest old brick buildings, and you learn the significance of local food, history, and culture of this area.

Enjoy the car-free carriage roads at a comfortable pace on a ranger-guided 6.0 mile moderate ride while discovering the diverse beauty of Acadia. The program price includes the use of a 21-speed bike and helmet for the full day. Bonus: If you'd like to continue carriage road exploration, keep your bikes through the end of the day at no additional charge!

Active travelers will love cycling along the New Hampshire coastline without the risk of getting lost. On this small-group tour you’ll cycle more than 17 miles through villages, past historic sites, and to beautiful beaches and viewpoints. This tour suits travelers with biking experience, letting you go at your own pace and enjoy the ride.

Arrive 30 min. prior to start time. This bike tour experience seamlessly blends history, art, culture, and local Portsmouth stories. This tour is guaranteed to satisfy your love of culture, history, and preservation. You and your guide will ride 6-8 miles in Portsmouth, into quiet, tucked-away neighborhoods, stopping at historic landmarks. Your guide will share fascinating stories about the maritime history, fishing, and the historic preservation that paved the way for historic House museums, and Strawbery Banke: a collection of preserved 18th-20th century homes during Urban Renewal. -Pedal to the North End and hear the stories that bring this former neighborhood to life -Visit The Hill, where 19th-century homes were saved and moved during Urban Renewal -Explore the riverfront of Prescott Park a former run-down neighborhood turned into a performance hub -Pedal to Little Harbor and hear stories about the royalty at the Wentworth‑Coolidge Mansion -Visit the runaway Ona Judge mural

Take a leisurely ride through Boston on the on this 2.5-hour cycling tour. Take in the Boston skyline, ride along the banks of the Charles River, and learn about Cambridge and Boston's history through your guide's commentary. Suitable for families with young children, this tour includes use of bike and helmet.

Experience the best of Nantucket with this 2-in-1 bundle — two complete self-guided tours available together at a discounted price. Begin your adventure with a walking tour through the heart of downtown Nantucket, learning about the whaling trade, and discovering landmarks like the Atheneum and Hadwen House. Next, embark on the Nantucket Coast to Coast drive or bike tour, stretching from Madaket to Sconset. Follow a scenic route past windswept beaches, historic lighthouses, and classic shingle cottages that reveal the island’s more tranquil side. Each tour is available separately, but when purchased together, they offer a flexible and memorable way to explore the entire island at a discounted rate. - Two complete self-guided tours at a discounted bundle price - Walking tour through downtown Nantucket’s historic sites - Scenic drive or bike tour from Madaket to Sconset - GPS-triggered audio works offline - Discover hidden gems and learn about the island’s maritime heritage

This 10-mile non-electric bicycle tour includes stops at all the scenic and historical highlights of the Kennebunk and Kennebunkport areas. You’ll get up close to a 19th-Century shipbuilder’s home, view breathtaking seascapes, tour a stunning seaside chapel, marvel at the sweeping compound of two American presidents, and gaze at a classic Maine lighthouse — among many other points of interest. The route itself is worth the ride: one of the most iconic coastal byways in Southern Maine. All your guides are locals, with deep knowledge of the region’s history and culture and a gift for storytelling. We love talking about this area, and we will be happy to answer any questions you might have along the way. The bikes themselves offer pure, human-powered, eco-friendly enjoyment — maintained to the highest standards by expert mechanics. You can choose from an 8-speed cruiser bike with swept-back handlebars or a sportier hybrid. Smaller bikes are available for younger participants.

Highlights: • Immerse yourself in New Hampshire’s spring and summer foliage, pedaling through vibrant woods and serene marshes. • Enjoy a peaceful, car-free ride along the scenic New Hampshire Greenway, perfect for families and nature lovers. • Spot wildlife along the trail, from turtles and wild turkeys to familiar songbirds in their natural habitat. • Ride easily on flat, well-maintained crushed stone and gravel paths, ideal for a relaxing and stress-free cycling adventure. • Take in quiet wooded clearings and winding marshside paths, the perfect escape from city life and daily routines. Enjoy a peaceful ride along the scenic Greenway on this guided rail trail tour. Pedal through tranquil natural landscapes as you follow a former railroad corridor known for its flat, easy riding and relaxing atmosphere. Led by an expert guide, you’ll ride approx. 14+ miles along a crushed-stone trail, passing wetlands, wildlife, and wide-open clearings. This is a great way to unplug and reconnect.

Uncover the hidden corners and rich history of Nantucket on this self-guided driving or biking tour (does not include rental). From lighthouses and historic homes to pristine beaches and iconic vistas, this tour offers a comprehensive exploration of the island's unique character. Learn about Nantucket’s culture and history as you ride (or drive) across the island, from Madaket to Sconset. We’ll point out several points of interest along the way as you explore Nantucket from coast to coast. Need a bike? We recommend Young's Bike Shop (on Broad St.) or Cook's Cycles (on S Beach St.). You will need to contact them directly to arrange your own rentals separately.

Explore Portsmouth, New Hampshire on two wheels with this half-day, self-guided e-bike or bike rental. Choose your own pace and cycle between landmarks at your leisure. See local sites like Prescott Park, Fort Stark State Historic Site, and the Wentworth-Gardner House. Plan your own itinerary and cover ground quickly on a comfortable 7-speed bicycle. This rental includes a map, lock, and helmet.

Discover Boston’s fall beauty on this guided, 4-hour, small-group bike tour around the North End of the city. Explore the historic Emerald Necklace, a 1,100-acre chain of parks linked by parkways and waterways in Boston and Brookline. Visit the shaded boulevard on Commonwealth Avenue, the shores of Jamaica Pond, and the popular, winding paths of the Arnold Arboretum of Harvard University. Also, see the Rose Kennedy Greenway, Boston’s newest public park; the famous Charles River Esplanade; the Boston Common and Public Garden and much more.

Discover Provincetown from a new perspective with our Private Open-Air Pedicab Tours. Relax in comfort as our knowledgeable guides lead you through the charming streets and scenic coastline of this historic town. Enjoy unobstructed views and personalized insights into local history, culture, and hidden gems that only a pedicab can offer. Whether you're captivated by the natural beauty or intrigued by Provincetown's rich heritage, our tours provide a unique and eco-friendly way to experience all that this vibrant destination has to offer. Unlike large bus or group tours, pedicab tours provide an intimate experience with a knowledgeable driver who can tailor the time to your interests. You can ask questions, engage in conversations, and make specific requests. Pedicab tours can be customized to your preferences and schedule. Choosing a pedicab tour contributes to sustainable tourism practices and minimizes your carbon footprint.