Exploring Maine Peninsulas:
An Essential Checklist

Stretch your legs or stretch out on the beach. Go on a gallery crawl or go to town on a lobster roll. Hitch a ride on a ferry or cruise down country roads. But most of all, relax, smell that salt air, and savor the trek along the midcoast’s jagged, lush, breathtaking coastline.

[cs_drop_cap letter=”A” color=”#560000″ size=”5em” ]ll it takes to ditch summer traffic on Route 1 is a quick turn down one of the midcoast’s peninsulas. The pace is slower, the atmosphere quieter. Uncrowded trails, idyllic lobster shacks, world-class arts venues, quaint shops, and dramatic lighthouses dot the landscape. Along a 50-mile stretch of Route 1 between Brunswick and Rockland, the seven long, narrow promontories dangle off the mainland like rips in Maine’s geological fabric, beckoning travelers to detour down winding, congestion-free roads. Whether you visit for the day or stay for the week, any one of these peninsulas offers enough intrigue, beauty, and adventure to keep you coming back time and time again.


An easy day trip from greater Portland, the drive to Harpswell offers a restful break from peak-season crowds, with tranquil nature trails, great eats, and a surfeit of stunning coastal scenery.

Take a Hike

Dozens of miles of trails meander through Harpswell’s pine forests and along its craggy shoreline. The Cliff Trail (263 Mountain Rd.) is a 2.3-mile loop that follows a tidal creek then climbs to the top of a 150-foot cliff above Long Reach. On 118 acres of woods, fields, and rocky outcroppings, Bowdoin College’s Coastal Studies Center (240 Bayview Rd.) offers a never-busy trail network along Harpswell Sound. And for sheer gravitas, the half-mile stroll at Giant’s Stairs (19 Ocean St.) shows off the ruggedness of Casco Bay, especially when seas are high and waves break on the rocks below.

Go Cruising (on Dry Land)

Driving on the Harpswell Peninsula and its adjacent islands — Orr’s and Bailey, both accessible via bridge — yields countless views of quiet coves and beaches on account of how slender the land is here. You’re never more than a stone’s throw from the water. All you have to do is roll down the windows, feel the breeze, and drive until the road dead-ends at the sea. On Bailey Island, that liminal point is Land’s End (2391 Harpswell Islands Rd.), where you’ll find a gift shop, a pocket beach, and a bronze lobstermen memorial statue, modeled after a local lobsterman, a copy of which resides on Maine Avenue in Washington, DC.

Make a Picnic

There are half a dozen idyllic spots to eat a lobster roll in Harpswell, but for a change of pace you might consider assembling a meal of your own. Black Sheep Wine & Beer Shop (105 Mountain Rd.; 207-725-9284) sells locally made and imported cheeses, crackers, salami, mustards, fruit spreads, and chocolates — just about anything you could need for the perfect picnic. And you’ll have your choice of scenic venues — Stover’s Point Preserve (69 Windsor Ln.) is an especially nice spot to grab a bench or spread a blanket on the sandy beach.

Marvel At an Engineering Feat

The Bailey Island Bridge — more commonly called the Cribstone Bridge — is a one-of-a-kind. Built in the 1920s, it’s the only such bridge in the world, with a latticework of huge granite blocks held together by gravity, supporting the road above. The impetus behind the unusual structure — besides to connect Bailey and Orr’s islands — was to create something that could withstand — and not inhibit — the constant ebb and flow of tides. All that marveling got you hungry? Cook’s Lobster & Ale House (68 Garrison Cove Rd.; 207-833-2818) and Morse’s Cribstone Grill (1945 Harpswell Islands Rd.; 207-833-7775) are great stops for a bite right by the bridge.


Maine’s loveliest beach? A short boat ride to an island lighthouse? An unbeatable breakfast? It’s easy to pass a day on the Phippsburg Peninsula — and hard to convince yourself to leave.

Have a Beach Day

Maine’s most popular sandy beaches are concentrated south of Portland and encircled by real estate and commercial development. But Popham Beach State Park (10 Perkins Farm Ln.; 207-389-1335) is arguably home to Maine’s finest sandy strand, and there’s hardly a man-made structure in sight — only pine groves and dunes. On weekends, the parking lot can fill up fast, but no matter how busy it seems there on the pavement, you never have to jockey for real estate on the enormous beach. You can be sure it’s not those deli subs. At low tide, it’s fun to walk out to Fox Island for a scramble on the rocks and a closer view of the islands and ocean beyond.

Visit an Island Lighthouse

Midcoast peninsulas are punctuated by many a beautiful lighthouse, but not a one feels more remote than Seguin Island Light Station (207-443-4808) and not a one is taller — top to bottom, Seguin is the biggest beacon in Maine. Visitors can spend several hours admiring the beacon and the tramway used to shuttle supplies up the long slope from the water as well as wandering the island trails. Boat owners have the option to pilot themselves out, but most visitors take the ferry (207-841-7977) from Fort Popham (10 Perkins Farm Ln.; 207-389-1335), a Civil War-era defense at the mouth of the Kennebec River that’s worth exploring too.

Start Your Day Right

The beginning of any drive down the peninsula leads past one of the midcoast’s quintessential eateries, Winnegance Restaurant & Bakery (36 High St., Bath; 207-443-3300). Housed in a century-old general store building, the dinette opens at 6 A.M. every day to serve the classics — eggs, bacon, pancakes — and more creative, coastally influenced numbers — pan-blackened haddock omelets, Cajun scallop breakfast tacos, crabmeat scrambles. If you got a late jump on the day, worry not: lunch fare follows the same classic/creative formula. On a sunny day there’s no better perch to enjoy a meal than from the store’s front porch, with its picture-perfect water view.

Take Your Own History Tour

Much of Phippsburg’s history hides in plain sight. A shipbuilder’s mansion has become a bed-and-breakfast. The old stone schoolhouse is now a private home. WWI and WWII coastal fortifications lie just up a footpath from the site of the first English settlement attempt in New England. It would be tough to track down each of the dozen or so historical points of interest scattered around the peninsula if the Phippsburg Historical Society hadn’t conveniently designed a self-guided driving tour that just so happens to be incredibly scenic too. Along the way, visit the historical society’s small museum (24 Parker Head Rd.; 207-389-2393) to check out collections of clothes, tools, furniture, and other artifacts that document, as museum literature puts it, “the customs, modes, and habits of Phippsburg.”


Home to Maine’s first publicly owned saltwater beach — plus a beloved seaside eatery, delightful shops, and more — Georgetown Peninsula has a knack for rewarding relaxation-seeking travelers.

Get Your Claws Out

You can’t get lost on the way to Five Islands Lobster Company (1447 Five Islands Rd.; 207-371-2990). After turning off Route 1 for Route 127, you don’t need to turn again. Just drive until the road intersects Sheepscot Bay. There, the lobster shack’s deck — an active fishing wharf — beckons with incredible scenery of moored boats bobbing in the foreground, wooded islands filling the background. The lobster is fresh as can be, and the kitchen is especially adept with the fryer, so add some fried clams and onion rings to your order. And since it’s a BYOB operation, swing by Georgetown Country Store (769 Five Islands Rd.; 207-371-2106) on the way for a sixer of Maine brew.

Warm Up, Cool Off

A beach trip is even more rewarding when you feel like you’ve earned the right to stretch out on a blanket, pull a hat over your eyes, and doze to the rhythmic wash of the waves. Reid State Park (375 Seguinland Rd.; 207-371-2303) has a popular beach — the first saltwater beach in Maine to become a state park — but it also has several miles of trails to explore before hitting said beach. An easy 2-mile loop leads to a pond and bog, across the road from which is an old one-room schoolhouse. Another pleasant trail traces the bank of the Little River, a popular venue for birdwatchers.

Eat Up History

The post-and-beam, mid-1800s Robinhood Free Meetinghouse (210 Robinhood Rd.; 207-613-5682) started its life as a church. More recently, it was a destination restaurant popular for its creative fare and rustic setting. Two years ago, though, the place was sitting empty when Ali and Carlos Barrionuevo moved from Washington, DC, and reopened it as an event space and breakfast spot. On weekdays, they serve coffee and pastries. Sunday brunch gets more elaborate, with Belgian waffles, mushroom toast, fried oysters, mimosas, and more. At night, it often turns into an uber-atmospheric venue for live music.

Shop, But Don’t Drop

Part of the beauty of midcoast peninsulas is just how non-commercial they feel — no garish kitsch emporiums lining the roads. Businesses in Georgetown are best browsed at a leisurely pace. Besides flowers, fresh produce, and picnic fare, Five Islands Farm (1375 Five Islands Rd.; 207-371-9383) sells charming gift items, like kitchenware and garden décor. And Georgetown Pottery (755 Five Islands Rd., 866-936-7687) has been making gorgeous, hand-painted porcelain pottery for the better part of five decades, covering pretty much any household need, from candlesticks to lamps, and from serving bowls to sink basins.


Boothbay Harbor is one of the state’s buzziest summer towns. That energy radiates around the peninsula, in the form of museums, galleries, and restaurants, but there’s plenty of peace and quiet to uncover too.

Smell the Flowers

The midcoast is jam-packed with natural beauty — but for a sampling of cultivated beauty, Coastal Maine Botanical Gardens (132 Botanical Gardens Dr.; 207-633-8000) is as popular with serious green thumbs as with families looking for a leisurely outing. Sprawling over some 300 shoreline acres, the gardens comprise swaths of rhododendron, trillium, peonies, hydrangea, hosta, water lilies, and much more. Plus, there are woodsy trails, ponds, and a butterfly house. And the on-site cafe is a serene spot for a wholesome sandwich or salad or for a quick drink or snack.

Nosh Like a Local

Away from the bustle of Boothbay Harbor, Southport General Store (443 Hendricks Hill Rd., Southport; 207-633-6666) epitomizes the Maine general store. It’s a tidy, efficient place to pick up necessities — and it has a heck of a lunch counter. Drive your tuna melt or meatball sub another half-mile to Hendricks Head Beach (Beach Rd., Southport), where you can grab a spot on the rocks and enjoy your sandwich with a dramatic view of the privately owned Hendricks Head Light. Or if you’re in the mood for more unusual fare, check out the menu at East Boothbay General Store (255 Ocean Point Rd., East Boothbay; 207-633-7800): options like banh mi, buffalo cauliflower wraps, and Tuscan chicken panini.

Do an Art Crawl

Boothbay Harbor boasts a dense cluster of first-rate art galleries, including Gleason Fine Art (31 Townsend Ave.; 207-633-6849), specializing in 19th and 20th century works, Studio 53 Fine Art Gallery (53 Townsend Ave.; 207-633-2755), with an emphasis on showing contemporary artists, and the Boothbay Region Art Foundation’s gallery (1 Townsend Ave., 207-633-2703) featuring the organization’s member artists. Whether you’re looking to buy or just browse, ducking in and out of galleries is a great way to explore town. Throughout the summer, a number of galleries participate in the monthly First Friday Art Tour, hosting free public receptions and demonstrations.

Hitch a Ride

At the height of Maine’s lumber industry, constructing full-scale railroads to haul workers and supplies would have proven too costly in many reaches of the state. Instead, companies opted for narrow-gauge lines, with two-foot-wide tracks. Most all of that old rail network has disappeared, but you can still hop aboard a classic two-footer at the Boothbay Railway Village (586 Wiscasset Rd., Boothbay; 207-633-4727) for a historical ride. The museum also hosts antique railroad memorabilia, a model railroad, and exhibits about life in 18th- and 19th-century Maine and about the advent of the automobile.


From the gem of a downtown just off Route 1 to the cluster of marquee sights at its tip, the rolling, winding Pemaquid Peninsula is a must-see destination from top to bottom.

Go Farther

The small coastal village of New Harbor already feels pretty off the beaten track. But once you’re done exploring the village, hop the ferry (129 State Rte. 32; 207-677-2026) in the harbor and head 10 miles out to sea to reach Monhegan Island. The journey makes for a day trip or an overnight at one of the island’s several guesthouses, including the timeless Island Inn (207-596-0371). While you’re there, take in the nature trails, the windswept cliffs, and the quietude — and grab a beer at Maine’s most out-of-the-way brewery, Monhegan Brewing Company (1 Boody Ln., 207-596-0011).

Stop Through the Twin Villages

North–south travelers on Route 1 are missing out if they cruise past the exit for Damariscotta and Newcastle, the Pemaquid Peninsula’s side-by-side gateway villages. There are so many great eats right downtown: pub-style fare at Newcastle Publick House (52 Main St., Newcastle; 207-563-3434) and King Eider’s Pub (2 Elm St., Damariscotta; 207-563-6008), chefy offerings at Van Lloyd’s Bistro (85 Parking Lot Ln., Damariscotta; 207-563-5005), classic and creative lobster rolls at Joe Lane Lobsterman (115 Elm St., Damariscotta; 207-682-0110), and oysters galore at Shuck Station (68 Main St., Newcastle; 207-682-0129). Plus, the Damariscotta side of the two villages boasts a classic old theater, a charming general store, a cozy bookshop, and an unbeatable setting along the Damariscotta River, where some of Maine’s finest oysters grow. Hop aboard a Damariscotta River Cruise to see it close up.

Explore the Point

It’s well worth the half-hour drive all the way out to the tip of the peninsula, where visitors are treated to a trifecta of sights. Pemaquid Point Light (3115 Bristol Rd., Bristol; 207-563-1800) strikes such an impressive pose that it wound up gracing the U.S. Mint’s Maine State Quarter. Just back up the road is Pemaquid Beach (Pemaquid Beach Park, New Harbor; 207-563-1800), a fine stretch of sand for lazing the day away, and Colonial Pemaquid State Historic Site (Colonial Pemaquid Dr., New Harbor), where visitors can check out a reconstruction of Fort William Henry and ponder artifacts from 17th- and 18th-century life on a site where colonists and native tribes often clashed.

Go For a Paddle

Maine’s peninsulas are great for exploring by kayak, with mile upon mile of rocky, wooded shoreline chock-full of wildlife. Much of these coastal waters is sheltered from the open ocean, which makes for calm paddling, but be sure to know what you’re doing before venturing out. If you’re a novice paddler, you might want to take a tour with an outfit like Maine Kayak Rentals (113 Huddle Rd., New Harbor; 207-677-3455) or Midcoast Kayak (47 Main St., Damariscotta; 207-563-5732), which provide gear and pointers and offer everything from guided sunset paddles to full-day adventures.


Split between the towns of Cushing and Friendship, this rural, little-traveled area is fertile ground for discovery, whether it’s a classic sandwich, an off-the-wall beer, or a whole new view of famous artists.

Step Into Art

A humble farmstead where siblings Alvaro and Christina Olson lived, the Olson House (318 Hathorne Point Rd., Cushing; 207-596-6457) provided inspiration and subject for much of painter Andrew Wyeth’s most famous work, including Christina’s World. Wyeth’s depiction of Christina, plagued by a degenerative disorder, dragging herself back toward the house has resonated with viewers for 70 years. Now, the home is open to the public, run by Rockland’s Farnsworth Art Museum, a repository of many Wyeth works. Largely unchanged since Wyeth’s days, the house provides an opportunity to see what the painter saw — and maybe even to feel some of what he felt.

Order a Proper Maine-style Italian

In many quarters of the country, an Italian sandwich means a pile of various cured meats: salami, mortadella, capocollo. Here, an Italian is a simpler matter — and many a Mainer would argue all the better for it. The only protein is plain ol’ ham. Traditional toppings are cheese, black olives, green peppers, tomato, pickles, and onion. All of that gets wedged inside a sub-style bun. Salt, pepper, and oil are optional. Nary another joint knows its way around the classic as well as Wallace’s Market (11 Harbor Rd., Friendship; 207-832-2200), the peninsula’s go-to joint for takeout, groceries, fishing gear, you name it.

Grab a Drink

Turning off Route 1 in Waldoboro to head down the peninsula, you’re a half-mile detour from one of the midcoast’s newest, most avant-garde breweries. The husband–wife duo behind Odd Alewives Farm Brewery (99 Old Rte. 1, Waldoboro; 207-790-8406), which opened this spring, does unusual things like trimming blossoms from their hundred-foot lilac hedge and adding them to a brew. The gorgeous pastoral setting, complete with patio, lawn, and horseshoe pits, is the perfect place to relax and contemplate the creative concoction in your glass.

Stroll Through an Art Park

Andrew Wyeth wasn’t the only artist smitten by the pastoral life in Cushing. Renowned sculptor Bernard Langlais produced many of his angular, colorful, larger-than-life sculptures on his homestead there. Part of that land opened to the public last year as the Langlais Sculpture Preserve (576 River Rd.; 207-594-5166), an open-air museum showcasing a dozen works, including a tongue-in-cheek monument to President Richard Nixon, a 13-foot-tall horse, and, in a fitting homage, the figure of Christina Olson straining to reach her home, a 10-minute drive farther down the peninsula.


A short drive from bustling Rockland leads to a world-class collection of cars and planes, too many great lobster shacks to choose from, and a site with serious Hollywood cachet.

Follow Forrest

Marshall Point Light (Marshall Point Rd., Port Clyde; 207-372-6450) looks like one of the Maine coast’s humbler beacons, barely poking out at the end of a long wooden walkway. But Forrest Gump fans might recognize the diminutive lighthouse as the place where the titular character’s cross-country run ended on the East Coast. Today, visitors wander the shore to find just the right angle for photographing the Hollywood-famous light — and if you hang out awhile, you’ll see many a person decide to make like Forrest, jogging across the walkway for cinematic effect.

Find Gearhead Mecca

Aficionados of old-time automobiles and airplanes can poke around the Owls Head Transportation Museum (117 Museum St., Owls Head; 207-594-4418) for hours. Adjacent to Knox County Regional Airport, where Cape Air flights shuttle to and from Boston, the museum has a collection spanning from a 1900 bi-wing ornithopter (one of those crazy contraptions with wings that flapped like a bird’s) to midcentury single-props and from an 1886 Benz motor carriage to a 1955 Ford Thunderbird. Nearby, the airport’s unexpectedly gourmet cafe, the Salty Owl (23 Terminal Ln., Owls Head; 207-594-0018) is a fun place to watch modern-day planes come and go and to enjoy a savory hand pie, a polenta bowl, or a homemade pop tart.

Make a Tough Decision

The St. George Peninsula has an embarrassment of lobster-shack riches. McLoons Lobster Shack (315 Island Rd., Spruce Head Island; 207-593-1382) is on an island beyond an island, connected to the mainland via causeway. There, you can — and should — get a lobster roll with both mayo and butter. Luke’s Lobster (12 Commercial St., St. George; 207-828-4882) might sound familiar even if you’ve never been. That’s because it now has locations across the country (and in Japan), but it all started here at the ever-popular original. And near Drift Inn Beach — a peaceful, out-of-the-way patch of sand — is Drift Inn Canteen (686 Port Clyde Rd., Tenants Harbor; 207-372-2068), where everything from the arugula salad to the lobster roll to the pulled pork is done just right.

Hang Out in Port Clyde

The picturesque huddle of buildings that forms Port Clyde is at the literal end of the road. But despite the location, the little village bustles with activity. You can sip a seaside cup of joe from Squid Ink Coffee (6 Cold Storage Rd.; 207-372-2088), grab a bite by the docks at the Dip Net (4 Cold Storage Rd.; 207-372-1112), or stroll with a cone from Village Ice Cream & Bakery (875 Port Clyde Rd.; 207-372-6479). There’s also Linda Bean’s Maine Wyeth Gallery (4 Cold Storage Rd., second floor; 207-542-8356), with paintings and prints from multiple generations of Wyeth painters, from N.C. to Andrew to Jamie. Plus, in Port Clyde, as in New Harbor, you can catch a ferry to Monhegan Island (880 Port Clyde Rd., 207-372-8848).


Keep Exploring!

For more ideas about midcoast peninsular adventures, check out the trip-planning resources at the Maine’s MidCoast & Islands website.