Guide to the Maine Peninsulas | Where to Play, Eat, Shop, and Stay

In the 2016 Yankee feature “A World of Their Own,” we set off on a five-peninsula-hopping expedition in Maine’s Casco Bay. The wildly beautiful Maine Peninsulas invite ambling and stopping, so it’s no surprise that they’re also home to many wonderful places to eat, shop, and stay. Read on for a list of some of our favorite spots along Maine’s beautiful Harpswell, Phippsburg, Georgetown, Boothbay, and Pemaquid Peninsulas.

Harpswell Peninsula

Things to Do

Eagle Island Robert Peary’s island in Casco Bay, aboard the Marie L. H2Outfitters (Orr’s Island) One of Maine’s oldest kayak outfitters; lessons, guided trips. Casco Bay Lines (Bailey Island) Noontime cruise from Cook’s Lobster House past Eagle Island and Mackerel Cove. Giant Stairs (or Steps) Epitome of rocky-coast drama and crashing waves; nice walk.

Places to Eat

Dolphin Marina & Restaurant, Harpswell Views from the tip of Basin Point. Cook’s Lobster House, Bailey Island Lively favorite on a cottage-dotted spit of land. Morse’s Cribstone Grill, Bailey Island Fresh seafood on a long pier.

Places to Stay

Harpswell Inn Richard and Anne Moseley’s eight elegant guest rooms. Driftwood Inn & Cottages, Bailey Island Oldest inn on island, overlooking Little Harbor.

Phippsburg Peninsula

Just past Bath, Route 209 South twists by lobster shacks, aging boats in backyards, and flashes of salt marsh that expand into vast plains, greener than any field. And when the road takes a turn, you’ll find its crown jewel: Popham Beach State Park.

If you don’t know how to eat a lobster, Spinney’s Restaurant, three miles away in the shadow of Fort Popham, on the banks of the Kennebec River, offers an instruction chart. You can also absorb visual pointers on how to build a spectacular driftwood fence, which is all that separates us from the sand and water. Bathrooms are labeled Buoys and Gulls (“You want the mermaid, hon”); the wood interior is draped with sea paraphernalia; and the haddock chowder is addictively good. Chunks of fish, potatoes, and a reddish tang of paprika: A second cup feels inevitable.

Civil War–era Fort Popham is weird and wonderful, like the bottom half of a more modern-day Colosseum. All archways, tunnels, and half-moon curves, it’s a haunting relic that echoes with children’s shouts and offers shade to fishermen casting their lines. The view across the water to Georgetown foreshadows our next stop, which is another poetic truth of peninsulas: You’re always looking over to the next point of land.

Things to Do

Sequin Island Light Ferry from Popham Beach to 186-foot granite lighthouse (tallest and second oldest in Maine) on 64-acre island. Seaspray Kayaking Kayak from Sebasco Harbor Resort. Rentals, instructions, tours, stand-up paddleboarding.

Places to Eat

Spinney’s Restaurant, Phippsburg Seafood by the fort.

Places to Stay

Sebasco Harbor Resort Family-geared 550-acre 133-room waterside resort. Hermit Island Campground 275 campsites at Small Point (tents and camper pickups).

GEORGETOWN PENINSULA

Things to Do

Coveside B&B Low-key canoeing from the dock to Five Islands Lobster Co.

Places to Eat

Five Islands Lobster Co., Georgetown Casual dining on the wharf. Grey Havens Inn, Georgetown Gourmet chef; outstanding water views from the porch (beautiful rooms, too).

Places to Stay

Coveside Bed & Breakfast, Georgetown Tom & Carolyn Church, innkeepers. The Mooring B&B, Georgetown Paul and Penny Barabe, great-granddaughter of Walter Reid, donor of the land for his namesake state park.

BOOTHBAY PENINSULA

Things to Do Monhegan Island The mecca of Maine islands for artists; Balmy Days Cruises. Burnt Island Lighthouse Tours with Dept. of Marine Resources aboard the Novelty. Cap’n Fish’s Boat Trips Whales, puffins, or sunset sail. Coastal Maine Botanical Gardens 270 acres of tidal shoreland; 16 years of planting.

Places to EatThe Lobster Dock, Boothbay Harbor In-town lobster near the footbridge. Ports of Italy, Boothbay Harbor Pretty and upscale, serves pasta with seafood. The Boathouse Bistro Tapas Bar & Restaurant, Boothbay Harbor Tapas on the top floor with a view. Places to StaySpruce Point Inn Resort 57 acres on the water near Boothbay Harbor downtown; saltwater pool, hot tub. Boat to town. Linekin Bay Resort Last all-inclusive sailing resort on the East Coast, family-owned since 1909; 20 acres on the bay. Gray Homestead Oceanfront Camping, Southport Camping, cottages, and condos, with private beach.

Pemaquid Peninsula

Things to Do

Hardy Boat Cruises New Harbor to Monhegan and Egg Rock (puffins). Maine Kayak, New Harbor Between Muscongus Bay and Johns Bay, with guided kayaking, plus eco-tourism.

Places to Eat

Pemaquid Lobster Co-op Restaurant, Pemaquid Harbor Operated by Pemaquid Fisherman’s Co-op, Maine’s oldest continuously run fishermen’s co-op. Shaw’s Fish & Lobster Wharf, New Harbor Classic lobster pound on picturesque harbor. Muscongus Bay Lobster, Bristol mainefreshlobster.com Round Pond Lobster, Round Pond facebook.com/Round-Pond-Lobster-181394501159Island Grocery, South Bristol Store/café on Rutherford Island, serving summer visitors since the 1800s. Pemaquid Oyster Co., Waldoboro Look for Damariscotta oysters—part of a 2,000-year-old tradition of eating briny things—at Maine coast seafood markets and restaurants (retailers list at website).

Places to Stay

Bradley Inn, New Harbor Culinary reputation; less than a mile from Pemaquid Lighthouse. Inn at Round Pond, Round Pond Stay in a picturesque waterside village. Thompson House & Cottages, New Harbor 21 cottages, many with ocean views.