Road Trip: The Maine Lobster Trail: Day 3

From Waldoboro to Vinalhaven Island via the lighthouse at Pemaquid Point, a convict craft shop, and a top New England art museum in Rockland

Pemaquid Point, Maine.
Pemaquid Point, Maine.

We fortified ourselves for the day with the $2.99 breakfast special at Moody’s Diner—typical, hearty diner fare of two eggs, two pancakes, and bacon—before heading down yet another long peninsula to my favorite spot on the Maine coast, Pemaquid Point.


Tip: You can rent the second floor of Pemaquid Point's 1857 lighthouse keepers house! It sleeps four (if you count the fold-out sofa) and costs $1,150 per week, plus a $55 cleaning fee:

This gorgeously eroded tongue of granite has a real land’s-end feel to it, sloping from a squat, whitewashed 1835 lighthouse down into the crashing waters of the Atlantic. We whiled away a good two hours scrambling over the rocks, peering into tide pools scuttling with tiny crabs, and simply gazing at the ocean's distant horizon.
Just up the road, we found a place that beat out Cook’s for the title of “most atmospheric lobster pound”: Shaw’s Fish & Lobster Wharf, a plank room with a sunny deck built out over a tiny cove bobbing with boats. We washed our lobsters down with pints of locally brewed Pemaquid Ale and Geary’s Summer Ale, and continued up the road to Thomaston and one of the oddest souvenir shops I’ve ever seen.

Fine arts and convict crafts

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

The Maine State Prison Showroom is a showcase for the handicrafts and woodwork of inmates in the state pen up the road in Warren. The prices were phenomenal—oak bookcases for $139, intricate wooden ship models from $69.

I am still kicking myself for not buying one of the birdhouses carved to resemble a jail, complete with “Maine State Prison” engraved above the perch and little bars on the windows. It was, however, a bit disconcerting to browse a store staffed entirely by convicts (plus a guard), especially when they ogled Frances as she walked past the check-out counter. (We both decided to take it as a compliment.)

The working port city of Rockland is slowly shaking off its rep as the Penobscot Bay’s industrial eyesore with the fleet of Windjammer sailing ships for hire, a proliferation shops and art galleries along Main Street, and above all the Farnsworth Art Museum.

This is one of the top art galleries in all of New England, stuffed with works by some of the greats of 19th century American art, including Winslow Homer, Thomas Eakins, and above all, the Wyeth clan—patriarch N.C. (famed illustrator of Treasure Island), son Andrew, who started the family’s habit of summering in Maine, and grandson Jamie.

The worship of the Wyeths is taken to literal extreme in the fact that the museum’s Wyeth Center is installed in a deconsecrated church behind the main building.

(More of Rockland's nearby sights, inclduing the Olson House featured in the famous Cristina's World painting, and the Mashall Point Lighthouse, are on Day 4)

The Oasis of Vinalhaven Island

Rockland was also the place to park our car and catch the ferry 15 miles (a 1-hour 15-minute ride) over to Vinalhaven Island, where we checked into an $85 room at the Tidewater Motel built right across the top of the roaring little stream that linked Carver’s Pond to Carver’s Harbor in the center of the main fishing village.

Actually, before we could check in we had to find the motel’s owner, Phil Crossman, who turned out to be across the street, chatting with folks amidst the flowers for sale in front of the Port O’ Call hardware store. He gave us a room with a picture window that opened onto a small deck and a sweeping view of Carver’s Harbor, flecked white with dozens of boats.

Phil lived next-door, and he had some rust-spattered Huffys out in the drive waiting to be cleaned up and put in service for the summer season. He lent us a couple, and we cranked the pedals laboriously a few miles out of town to Booths Quarry, the island’s swimmin’ hole.

Booth's Quarry swimmin' hole on Vinalhaven Island, Maine.
Booth's Quarry swimmin' hole on Vinalhaven Island, Maine.

It was sunny, but with a strong spring chill in the air, and the water felt about two degrees above freezing, but we saw some locals splashing around at the other end. I tried to convince Frances to jump in with me. “If a couple of adolescent girls can handle it,” I argued. “It can’t be that bad.”

What I failed to consider was that these girls had been tempered by Maine winters. I, on the other hand, was in for a Loony Toons moment: The second I hit the water, I levitated back out of it with a yelp and sprinted back along the surface to shore, purple-lipped and scowling at Frances, who was doubled over with laughter.

Once I thawed out, we biked back to Lane’s Island Preserve to watch the sun set over the mudflats and harbor beyond before returning for dinner at the Harbor Gawker, built onto a deck over Carver’s Pond, with white vinyl siding and a six-foot wooden cutout of a lobster nailed to the outside corner.

Sure, it was right across the street from our motel, but what really lured me in was the wipeboard sign advertising “Have a hunk of cornbread w/a slab of butter for $1.95.” I figured any place down-home enough to be proud of its cornbread and butter must be good.

Our crab roll and clam chowder were scrumptious, but we hadn’t known it was BYOB. So, after dinner we wandered up Maine Street to a no-name saloon, downed a quick bottle of beer, and went to bed lulled by the sound of water rushing under the floorboards.

Day 3 details


Tourist info

• Maine Office of Tourism,

• Rockland,,

• Vinalhaven,,,



• Pemaquid Point, 207-563-6246,, $2 parking fee.

Farnsworth Museum of Art, 16 Museum St., Rockland, 207-596-6457,, Closed Mon., $12 (free Sundays 10am–1pm).


• Maine State Ferry Service, Rockland, 207-596-2202,, $16 round-trip.


• Maine Prison Showroom, Route 1, Thomaston, 207-354-9237, open daily,


• Shaw’s Fish & Lobster Wharf, 129 Route 32, New Harbor, 207-677-2200, open late May–mid-Oct, around $10.25 for a lobster.
Harbor Gawker, Main St., Vinalhaven, 207-863-9365, $10.75 for a crab roll and clam chowder.


 Tidewater Motel, Vinalhaven Island, 207-863-4618,, Closed Jan–Feb, doubles $100–$195.

Waldoboro to Vinalhaven Island (65 miles)

• Start the day going backwards again, south on Route 1 to Damariscotta, and turn left onto Route 130 to Pemaquid Point.

• Driving back north up Route 130, in New Harbor veer right onto Route 32 to drive back north along the peninsula’s eastern shore back to Waldoboro, were you pick up (you guessed it) Route 1 again, headed north.

• It passes through Thomaston to Rockland. Park in the free lot; catch the ferry to Vinalhaven.



» Day 4: Vinalhaven Island to Camden via Rockport

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.