Road Trip: The Maine Lobster Trail: Day 1

From Portland to Westport Island via the DeLorme store in Yarmouth, outlets of Freeport (LL Bean anyone?), Wolfe's Neck Peninsula, and the Squire Tarbox Inn

Eartha, the largest globe on the planet, at teh DeLorme map headquarters in Yarmouth, Maine.
Eartha, the largest globe on the planet, at the DeLorme map headquarters in Yarmouth, Maine.

Before I left for Maine, I borrowed my Dad’s lovingly dog-eared DeLorme Atlas & Gazeteer of Maine—an incredibly detailed map on which he had highlighted his favorite drives and circled memorable towns and viewpoints in pen, with notes scrawled in the margins.

It was as good a resource as any guidebook—and any road trip done right bumps down back roads well off the interstate—but as this was to be my trip, not my dad's.

Mid-Coast Maine Road Trip
Day 1: Yarmouth, Freeport, and Westport Island
Day 2: Bath, Brunswick, Bailey Island, Damariscotta, & Waldoboro
Day 3: Pemaquid Point, Thomaston, Rockland, & Vinalhaven Island
Day 4: Rockland, Rockport, & Camden
Practical info

Second biggest globe on the planet

That meant our first order of business heading up U.S. Route 1 north of Portland was a stop in Yarmouth to get my own map in the shop at DeLorme headquarters.

The other reason to stop at this premier American mapmaker was the lobby, in which spins the largest globe on Earth (well, OK, second largest, if you count the Earth itself)—130 feet around, more than 41 feet high, and scaled to a mere one one-millionth of the planet’s actual size.

As I struck an Atlas pose for the requisite weight-of-the-world photograph, I though how brilliant it was of them to put in the topographical features, but leave off all political boundaries. This was the Earth as the astronauts see it, and all I could think was how mind-bogglingly big the Pacific Ocean truly was.

Sand dunes in Maine and a shopping mecca

The Desert of Maine outside Freeport
The Desert of Maine outside Freeport

Just south of Freeport we detoured for an irresistible dose of roadside kitsch: the Desert of Maine. This 40-acre plot of miniature sand dunes hemmed in by pine forest was formed in the early 1880s when over-farming depleted the thin layer of soil atop an ancient glacial deposit of sand.

It was quite striking to see—and terribly out of place in the North Woods—but the cheesy roadside attraction bells and whistles were a bit much: a miniature train to cart you around the dunes, staged gem hunts for the kiddies, plastic camels for photo-ops, and a nature trail through the wooded section that promised such wildlife wonders as “trees, birds, rabbits, squirrels, and chipmunks.”

Freeport, once a dying mill and industrial town, has revived as Maine's outlet shopping Mecca with more than 130 factory stores and specialty boutiques from Thomas Moser furnishings to discounted Clark’s shoes.

It all started with a single store: the 160,000-square-foot flagship of outdoors outfitter LL Bean, founded here in 1912 when avid outdoorsman Leon Bean perfected the waterproof hunting boot. The store has made an art form out of customer service: open 24/7/365, and promising to repair or replace any item at any time, no questions asked.

Not that they need to invoke that policy often.

Bean comes through
When I realized I needed to retire my old hiking boots—which were still in excellent shape; my feet had finally outgrown them—I went to a local sporting goods and camping store in Manhattan and tried on a dozen replacement pairs, and even wore several home.

None fit quite right, and with an impending weekend on the Appalachian Trail fast approaching, I returned them all and ordered a pair of old school, single-piece leather boots from LL Bean online.

They arrived the very afternoon I left for my trip, forcing me to commit the biggest no-no in hiking: hitting the trail in a pair of brand-new, un-broken-in boots.

Over two days I did 16 miles of Pennsylvania's gnarliest, rockiest trail—infamous as "the place where boots go to die" and the stretch that Bill Bryson skipped on his famous AT hike. I didn't even suffer a single hotspot, let alone get any blisters.

I don’t know how they do it, but Bean products are practically perfect.

Until my mid-30s—when I discovered that slowly expanding feet are a fact of aging—I still hit the trails in the hiking boots I had bought at Bean when I was 16 (see the box on the right). Frances told me that her mother’s “briefcase” is a canvas Bean tote bag that Frances’ grandmother bought in the 1940s.

(Fun fact: Bean actually invented the common tote bag. You probably never stopped to consider why the tote bag is such an unusual shape—wide but shallow—but there was a very good reason. It was originally called the "Ice Tote" and was sized for carrying home the slabs of ice used—back in the pre-Freon refrigerator days—to cool home ice boxes.)

Frances dragged me away from trying on Bean travel slacks to stroll a block and a half down Main Street to grab a table on the brick patio of the Lobster Cooker, a home-spun version of a fast food joint serving yummy lobster rolls—lettuce and lump lobster mixed with mayo on a hot dog bun.


Clamdiggers on Wolfe's Neck Peninsula, Maine.
Clamdiggers on Wolfe's Neck Peninsula, Maine.

After lunch we broke out our new map to explore Wolfe’s Neck Peninsula just across Harraseeket Bay from Freeport. The fog had rolled in thick by the time we reached the entrance to Wolfe’s Neck Woods State Park, so we skipped its hiking trails and veered east onto Burnett Rd.

The road quickly devolved into a dirt track and we got a postcard image of the old Maine that predates the outlet shops. At low tide, the sea along this coast recedes dramatically, turning Maine’s many little bays and river outlets into vast mudflats. As we crossed a wood plank bridge over the sluggish Little River, we saw hip-booted men scattered across the muddy bay, shrouded by thick mists and bent over double to dig for clams.

The ultimate country inn

Squire Tarbox Inn, a rambling 1763 farmhouse turned B&B, was so secluded that, by the time we finally found the place, we had already stopped twice by the side of the road to consult the map, convinced we had made a wrong turn. It was worth the search. Retired flight attendant Roni De Pietro showed us around the building and up an outdoor staircase to a bedroom with rough wood beams and a view over the sloping farm gardens to a pond-filled meadow.

A lounge in the 1763 farmhouse of the Squire Tarbox Inn in Maine.
A lounge in the 1763 farmhouse of the Squire Tarbox Inn in Maine.

After settling in, we returned to the inn’s little living room to nibble on fresh goat cheese, crackers, and olives while sipping red wine from the honor bar in the old butler’s pantry.

Squire Tarbox is as well known for its meals as its rooms, and for dinner Roni’s Swiss-born husband Mario—a veteran of 25 years in top New York kitchens (The Four Seasons, tavern on the Green, The Brasserie)—prepared a veritable feast.

We had mulligatawny (a kind of chicken curry soup from southern India; its name comes from the Tamil for "pepper water"), potato-crusted haddock, grilled salmon, and apple crumble.

Back in our room, I left the door open awhile just to enjoy the quiet and the darkness. A fluffy gray and white cat—named Molly, we discovered next morning—sauntered in, hopped up onto the bed’s patchwork quilt, and settled down to serve as our hot water bottle for the night.

Day 1 details


Tourist info

• Maine Office of Tourism,

• Freeport,


• DeLorme/Eartha, Two DeLorme Drive, Yarmouth, 207-846-7100,, free.
• Desert of Maine, 95 Desert Rd., Freeport, 207-865-6962,, open daily early May–mid-Oct, $8.75 (kids $5.75).
• Wolfe's Neck Woods State Park, 426 Wolfe's Neck Rd., Freeport, 207-865-4465 (off-season: 207-624-6080),, $1.50.


• LL Bean, Maine St., Freeport, 800-559-0747,, open 24/7/365.


• Lobster Cooker, 39 Maine St., Freeport, 207-865-4349,, lobster rolls about $14 (market prices; varies), other sandwiches $6.25–$10.50.
• Squire Tarbox Inn, 1181 Main Rd., Westport Island, 800-818-0626,, open mid-Apr–Jan 1 (Apr-May and Nov-Dec, inn guests can dine every night but passersby only Thurs-Sat) 3-course meal $40–$45.50.


• Squire Tarbox Inn, 1181 Main Rd., Westport Island, 800-818-0626,, Closed Jan 1–Mar 31, doubles $115–$199.

Portland to Westport island (55 miles)

• To save time, zip up I-295 to Yarmouth, then switch to US. Route 1, which follows the coast to become the main street of most major towns.

• In Freeport, head east on Bow St., right on Flying Point Rd., then right again onto Wolf’s Neck Rd. Turn left onto Burnett Rd., then right back onto Flying Point Rd. Fork left onto Casco Rd., right onto Pleasant Hill Rd., and left again onto Maine St. in Brunswick.

• Turn right onto Route 24/Old Bath Road, lined with classic 1950s-style burger joints, for the drive to Bath, where it joins up with Route 1.

• Continue north towards Wiscasset, but just after crossing Montsweag Brook, turn right into Route 144, which will dogleg left up Birch Point Rd., then right again onto Westport Island. Follow it until you see the Squire Tarbox Inn on your right.


» Day 2: Westport Island to Waldoboro via Bath, Brunswick, & Bailey Island

Tours Under $995 G Adventures

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This article was by Reid Bramblett and last updated in June 2012.
All information was accurate at the time.

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Copyright © 1998–2013 by Reid Bramblett. Author: Reid Bramblett.