Once ensconced on the coast of Maine, you’d be easily forgiven if you didn’t wish to do anything more strenuous than turn the pages of a book while lying in a hammock. But if you’re a back-roads adventurer, an outdoors enthusiast, or a connoisseur of gourmet meals, there are some additional interesting places to be found just a little bit farther afield.

Portsmouth, New Hampshire, for instance, is well worth a quick detour across the bridge from Kittery for its coffee shops, inns, boutiques, and pleasing snugness. Next, just inland from the midcoast section of Maine, huge Baxter State Park—featuring the lofty and impressive peak of Mount Katahdin—is one of Maine’s finest attractions, and a newly designated national monument is poised to become Maine’s next great outdoor playground.

Finally, coastal New Brunswick, an hour or less from Eastport, is worth seeing for its pretty seaside villages, islands, and high tides.

I have described each of these three side trips below, going in order from south to north.


Portsmouth is a civilized little seaside city of bridges, brick, and seagulls, and quite a gem. Filled with elegant architecture that’s more intimate than intimidating, this bonsai-size city projects a strong, proud sense of its heritage without being overly precious. Part of the city’s appeal is its variety: Upscale coffee shops and art galleries stand alongside old-fashioned barbershops and tattoo parlors. Despite a steady influx of money in recent years, the town retains an earthiness that serves as a tangy vinegar for more saccharine coastal spots. Portsmouth’s humble waterfront must actually be sought out; when found, it’s rather understated.

This city’s history runs deep, a fact that is evident on even a quick walk through town. For the past 3 centuries, Portsmouth has been the hub of the coastal Maine/New Hampshire region’s maritime trade. In the 1600s, Strawbery Banke (it wasn’t called Portsmouth until 1653) was a major center for the export of wood and dried fish to Europe.

Later, in the 19th century, it prospered as a center of regional trade. Just across the Piscataqua River in Maine (so important a connection that there are four bridges from Portsmouth to that state), the Portsmouth Naval Shipyard—founded way back in 1800—evolved into a prominent base for the building, outfitting, and repairing of U.S. Navy submarines. Today, Portsmouth’s maritime tradition continues with a lively trade in bulk goods; look for the scrap metal and minerals stockpiled along the shores of the river on Market Street. The city’s de facto symbol is the tugboat, one or two of which are almost always tied up in or near the waterfront’s picturesque “tugboat alley.”

Visitors to Portsmouth will discover a surprising number of experiences in such a small space, including good shopping in the boutiques that now occupy much of the historic district; good eating at many small restaurants and bakeries; and plenty of history to explore among the historic homes and museums set on almost every block of Portsmouth.


There are two versions of the Maine Woods. There’s the grand and unbroken forest, threaded with tumbling rivers, that unspools endlessly in the popular perception—and then there’s the reality. It’s tempting to see this region as the last outpost of big wilderness in the East, with thousands of acres of unbroken forest, miles of free-running streams, and more azure lakes than you can shake a canoe paddle at. A look at a road map seems to confirm this, with only a few roads shown here and there amid terrain pocked with lakes. Undeveloped, however, does not mean untouched.

The reality is that this forestland is a massive plantation, largely owned and managed by paper and timber companies large and small. An extensive network of small timber roads feeds off major arteries and opens the region to extensive cutting. In the early 1980s, New Yorker writer John McPhee noted that much of northern Maine “looks like an old and badly tanned pelt. The hair is coming out in tufts.”

Forest management practices are somewhat improved today; clear-cutting is diminished, although technological advances in logging have encouraged more rapid timber harvesting on the part of some companies (either to “flip” lands for a quick return or to pay down debts incurred as the forest products industry has waned). Still, timber and paper are no longer the boom industries they once were (Maine’s paper mills are shuttering at an impressive rate), and northern Maine has spent the last decade slowly embracing the potential of its recreation economy.

While the North Woods may not be a vast, howling wilderness, the region still has fabulously remote enclaves where moose and loon predominate, and where the turf hasn’t changed all that much since Thoreau paddled through in the mid–19th century and found it all “moosey and mossy.” So long as you don’t arrive expecting utter wilderness (on the scale of, say, the remote Rockies), you’re unlikely to be disappointed.

Once you’ve reached the northernmost limits of coastal Maine, it’s just a skip onward to the pleasures of maritime Canada. If you’re not hurting for vacation time, it’s worth packing your passport to spend a couple of nights in genteel, historic St. Andrews or the windswept world apart that is Grand Manan Island.

Whereas Campobello Island is essentially an afternoon jaunt from adjacent Lubec, the New Brunswick side of the Passamaquoddy region rewards deeper exploration, and it’s easy to reach by crossing the bridge over the St. Croix River at Calais, Maine, about a 40-minute drive north from Eastport.

The heart of the Passamaquoddy region is the briny Bay of Fundy, which is rich with plankton, and therefore rich with whales. Some 15 types of whales can be spotted in the bay, including finback, minke, humpback, the infrequent orca, and the endangered right whale. Whale-watching expeditions sail throughout the summer from Grand Manan, St. Andrews, and St. George. Any visitor information center can point you in the right direction.



Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.