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Cycle a picturesque coastal route from Gloucester to Maine

Cyclists on a Great Freedom Adventures tour from Massachusetts to Maine.Great Freedom Adventures

If you’ve ever dreamed of hopping on your bike and pedaling up the coast to Maine, but have no idea what route is best, where to sleep, or where to eat, you might check out Great Freedom Adventures.

Based in Sherborn and Woodstock, Vt., the adventure company creates bike tours, walking trips and multi-sport adventures around the United States and Belize. Its roster of guided New England bike tours includes a Massachusetts Beer Adventure Tour, Best of Vermont, Block Island Vacation Tour, and a Coastal Wine Trail Bike Tour, among others.

But if guides and groups aren’t your thing, the company has just created its first-ever self-guided Massachusetts-to-Maine bike route, encompassing some 455 miles of stunning New England seacoast from Gloucester to Bar Harbor, Maine.


Start on a date of your choosing. Rest when you want. Eat where you want. Pedal at your own pace. The company provides maps, cue sheets, area information, and will arrange accommodations. Go solo or with a group. Use your own bike or rent one from the company fleet.

Experienced cyclists — you’ll go some 50 miles a day — can embark on a nine-day, eight-night carefully mapped (i.e. safe, picturesque roads) ride through a cross-section of postcard-New England. If you don’t have nine days, no worries — you can also schedule to ride a certain portion of it.

The full route starts in Gloucester, cuts through swaths of New Hampshire, slicing through foodie cities like Portsmouth and Portland, past brake-worthy beaches, hugs the Maine Coastline up to Acadia National Park, and culminates with a sunrise push to the summit of Cadillac Mountain.

Great Freedom Adventures books your accommodations at a curated series of hotels. Your job each day, essentially, is to get from one to the next. There’s also a guided option, should that float your boat. Prices vary on a case-by-case scenario, dependent on a number of factors.


And if the length here sounds intimidating, they offer much shorter routes — think 6½ to 11 miles a day for three days on Block Island, or a similar workout on Martha’s Vineyard.

“There is nothing quite like traveling by bicycle. . . . It’s a transformative experience,” said Jeanne Rummel, founder and owner of Great Freedom Adventures, an avid cyclist who has been creating tours for some 40 years, including a decade at Great Freedom Adventures.

“You really see a place and that effectively imprints memories. It’s a tremendously satisfying feeling to travel completely under your own power.”

While she can’t give away the exact route — that’s part of what customers are paying for, after all — we asked about highlights of this new self-guided route, and about bike tours in general.

Q. What’s your favorite part of riding a self-guided bike tour?

A. The freedom. I love the fact that for that day, and each day of the tour, the only thing to be concerned about is getting from point A to point B. You’re focused only on that and on the beautiful and interesting things along the way. Everything else, all of the typical daily worries we all face, fades to the background. I find that liberating.

Q. What major cities or towns does the tour cut through?

A. The larger ones are Gloucester, Newburyport, Portsmouth, and Portland — and through many fun, smaller towns and fishing villages that epitomize quintessential coastal New England.


Q. What are some highlights?

A. Highlights are many: Gloucester’s Fisherman’s Memorial and Rocky Neck Art Colony. The Essex Historical Society and Shipbuilding Museum. All of Newburyport. Portsmouth’s Strawbery Banke. There are several lighthouses along the way. Lobster boats in harbors, and lobster pots on docks, are perfect photo ops. Acadia National Park and its Loop Road, Mount Desert Island, Bar Harbor, and Cadillac Mountain.

Q. Any good restaurants along the way?

A. Many! Portland is known for great restaurants — I particularly like Fore Street, Street and Co., and Scales. Gloucester has Seaport Grille on the water, and good beer and pub fare at Cape Ann Brewing. Woodman’s of Essex. Bar Harbor has all kinds of good options. In Portsmouth, N.H., The Library Restaurant has excellent food. Clam Box of Ipswich is a classic. Up in Castine, Maine, there’s great seafood. There’s so many little shacks along the route for lobster rolls. Damariscotta, Maine, has great cafes on the water.

Q. What stops would you suggest?

A. Stop in Newburyport and walk the charming streets and waterfront boardwalk. Stop in Portland and eat. Break for lobster rolls at every opportunity. Stop at art galleries and talk to artists. Stop at beaches to take a dip or just take in the view.

Q. What are some of your favorite day-stretches along this route?

A. I love the Blue Hill area of Maine and the Castine Peninsula. I designed the route to include a place where, when the tide is changing, you can jump off a bridge and ride the rapids.


Stretches through Essex, Ipswich, and Newburyport are gorgeous — salt hay farms, tidal inlets, lots of First Period colonial homes and sea captain’s mansions. I love Camden, Maine, and the harbor at Rockport, Maine.

Acadia is gorgeous, of course. And the early-morning bike to the summit of Cadillac Mountain to watch the sunrise is a pretty spectacular finale. When you get to the summit, you have a panoramic view of Frenchman Bay and the Porcupine Islands. You’re seeing the sunrise before anyone else in the country. If conditions are right, it bathes the area in a golden glow.

Q. Where do riders stay?

A. We have a list of inns that we can book for guests as part of the package. We design the route based on the area, the number of miles reasonable for most people to do each day, and to end up where there’s higher-end lodging, with restaurants to walk to, shops, pools, beaches — all the things people want on vacation.

Q. Do you offer easier tours?

A. Yes, we have tours that are appropriate for anybody. We have a three-day tours of Martha’s Vineyard and Block Island Tour that just about anyone can do. In all tours, guests bike at their own pace. Most are guided, so there would be a guide with them, sharing information along the way, and another guide driving the support van in the rear.


Q. How long does it take to map a route?

A. On average, a year. When you look at a map for a nice route, that’s not necessarily what pans out on the road. We want to make sure there’s a good shoulder, it’s safe, and it’s going through the most beautiful part of the countryside. Every mile has been biked or driven. We also look at rooms, see how clean and beautiful a place is, check the amenities.

Q. What other types of tours do you offer?

A. We offer bike tours in all New England States, New York, and New Mexico. We offer walking tours in Vermont, and multi-sport tours throughout the Northeast and New Mexico. Our Belize tour includes rain forest hikes, Mayan ruins, kayaking in the rain forest and ocean, snorkeling on the barrier reef, and more.

Contact info@greatfreedomadventures.com or call 508-545-1864. Learn more at www.greatfreedomadventures.com.

Interview was edited and condensed. Lauren Daley can be reached at ldaley33@gmail.com. She tweets @laurendaley1.