How to Plan an Epic Maine Road Trip: A Five-Day Travel Guide

Buckle up and let Maine's idyllic landscapes, epicurean gifts and exceptional hospitality guide you through an exhilarating escapade on four wheels.

Maine coast Boothbay Harbor with boats
A road trip to Maine is nothing short of magical. Universal Images Group via Getty

Nestled in the uppermost crest of the United States, Maine serves as more than a geographical milestone. Delving into Maine feels akin to wandering through Provence, a storied region in Southern France, brimming with countless rond-points. Each stop along the Pine Tree State’s main artery, Route 1, unfurls a new bouquet of delights, akin to the surprises that Provence’s labyrinthine roads reserve for those seeking out destinations like Arles or Saint-Tropez. However, over 300 miles driving the backbone of this New England state, you find yourself entranced not by glitzy French cities, but by quaint coastal hamlets, roadside seafood shacks and magnetic harbors that invite you to circle their virtues in awe and anticipation.

Picture getting swept up by Kennebunkport’s age-old allure, captivated by Portland’s pulsating heartbeat and spellbound by Boothbay’s quaint rusticity—all in one trip. Maine’s beauty, culture and gastronomy weave an irresistible spell that draws you to journey through its winding roads. Any seasoned local will assure you that a road trip is the premier path to excavating the region’s heart and soul. So, consider this the green light to start planning your getaway—a daily carousel of experiences crafting indelible memories. Buckle up and let Maine’s idyllic landscapes, epicurean gifts and exceptional hospitality guide you through an exhilarating escapade on four wheels.

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A sandy beach and clear teal waters with houses on the horizon.
Ogunquit. Paul Jebara

Day One: Kennebunkport and Ogunquit

Kennebunkport, a charming New England town, whisks you back in time with its old shipbuilder mansions narrating past tales. The Atlantic’s playful waves caress the shores alongside this postcard-perfect panorama. Dining is more an art than a meal, with places like The White Barn Inn serving culinary puzzles that unravel mouthwatering mysteries, while Clam Shack turns lobster into tantalizing symphonies of flavor.

Within a pebble’s toss, Ogunquit, a lively beach town, bursts with fervor come summertime. Despite housing fewer than a thousand inhabitants, it’s as dynamic as any sprawling metropolis. The town’s glorious three-mile-long sandy beach (you’ll appreciate the convenient beachfront parking), homestyle eateries and charming boutiques exude an infectious warmth. As the sun dips below the horizon, Ogunquit becomes an unexpected nightlife powerhouse. The Ogunquit Playhouse, a treasured relic from the “summer stock era” of the 1920s, underscores the town’s theatrical inclinations. Simultaneously, The Front Porch‘s patio becomes a magnet for conviviality, animated by the rhythmic harmonies of piano singalongs. End your night at the colossal multi-level nightclub Maine Street.

Where to stay: For a quintessential Maine experience, the Wanderer Cottages serve as an ideal home base. This collection of breezy beach cottages, each bearing a quirky name like “Love Shack,” radiate a retro appeal. Decked out with monochrome surf photography and nautical antiques, they provide a comforting retreat after a day of discovery.

Two close-ups of boats on the water.
Portland. Paul Jebara

Day Two: Portland

It’s about 50 miles from Kennebunkport to Portland, roughly an hour of driving, but oh, what an hour it is. Maine’s most populous city is a heady cocktail of creativity and decadence—both literally and figuratively as one of America’s next-gen culinary capitals. Kickstart your adventure at Miss Portland Diner, a historical gem. This 1949 dive, resplendent in its chrome-laced restoration, serves a nostalgic culinary journey that whisks you back in time. Maine blueberry pancakes drip with sweet memories, and comforting scallop casserole evokes the warmth of a grandmother’s cherished recipes.

As twilight blankets the city, Portland’s culinary scene steps farther into the spotlight. Central Provisions (lauded for the inventiveness of its small plates) and Eventide Oyster Co. (seafood, seafood and more seafood) are coveted mainstays—be sure to reserve in advance—while Highroller Lobster Co. remains the place to be for a low-key, high-fun meal out.

A teal oyster bar with fish in ice.
Eventide Oyster in Portland. Paul Jebara

Before setting your compass north, take a breather in Freeport (a mere 20 minutes from Portland), the birthplace of the iconic L.L. Bean flagship store. Far more than the purveyor of the legendary “bean boot,” this store caters to every Maine adventure, with cozy sweatshirts to stave off Atlantic breezes or robust tents for the audacious explorer.

The Press Hotel. Irvin Serrano

Where to stay: Housed in Portland’s former Herald headquarters, The Press Hotel brims with the energy of yesteryear’s newsroom. Every nook bristles with journalistic hints—from the typographic carpets to locally-sourced art. Union, the in-house restaurant, takes pride in showcasing seasonal produce, serving a parade of dishes made from the region’s finest harvests.

A dock with a sign reading "Lobster" leading out into green and blue waters, with a boat docked at the end.
Boothbay. Paul Jebara

Day Three: Boothbay

As you transition from one city to the next over the 70 miles from Portland to Boothbay, the changing landscapes provide a visual treat. The stretch of road from Portland to Boothbay clocks in at around 70. Dip your toes into the rustic charm of Boothbay—but not before you’ve savored a generous slice of Maine’s offerings at The Alna Store. Founded by husband-and-wife team Brain Haskins and Jasper Ludwig, this country store is a gastronomic tribute to Maine, an edible sonnet in honor of hyperlocal flavors. A world of globally-inspired provisions awaits behind its humble façade, along with a lunch menu skillfully composed. If you find yourself here on a weekend, you might be privy to a dinner soirée, an edible journey from the romantic landscapes of Spain to the sizzling allure of Szechuan spice. 

Flowers, grass, and trees surrounding a small lake.
Boothbay Botanical Garden. Paul Jebara

The Coastal Maine Botanical Gardens, a 250-acre living canvas of over 300 plant types, offers a verdant feast for plant lovers. Nearby attractions like the Boothbay Railway Museum and Boothbay Region Land Trust expand your exploration with glimpses into Maine’s rail history and hiking trails.

When hunger strikes (again), head to Shannon’s Unshelled for authentic Maine seafood or let Ports of Italy tempt you with exquisite dishes that weave local ingredients into Mediterranean melodies. If you can “bake” in more time to your itinerary, enlist Cabbage Island Clambakes for a windswept sail to Cabbage Island for a full-on seafood smorgasbord, New England-style. 

A mansion at dusk with orange lighting.
Topside Inn. Topside Inn

Where to stay: Perched majestically on a hill, Topside Inn sits inside a 19th-century sea captain’s home, gifting guests with a bird’s-eye view of Boothbay Harbor. A stone’s throw from the town center, it promises stylish solace in the main house and two delightful summer guesthouses. Each room, adorned with contemporary coastal decor, doubles as a welcome tonic to the day’s adventures.

A small town with red brick buildings and a blue sky above.
Camden. Paul Jebara

Day Four: Camden

Just about an hour from Boothbay, the town of Camden is sandwiched between the majesty of mountains and the magic of the sea. From the verdant Camden Hills whispering ancient stories to the lively Penobscot Bay, it’s a destination sure to enthrall explorers. Begin your day with a harbor walk before hitting the trails. Mount Battie offers a gentle climb with stunning harbor views. For thrill-seekers, Camden Hills State Park promises afternoon adventures.

Camden shows off its culinary charisma with beloved institutions like Uncle Willy’s Candy Shoppe and Peter Ott’s reigning as must-visits. The town embraces modernity as well, with innovative restaurants such as Long Grain and Natalie’s at the Camden Harbour Inn shaping your gastronomic journey, with the former crafting a poetic Thai culinary experience, while the latter harmonizes French finesse with Maine’s bountiful produce. 

A stone mansion with a cone-shaped turret, surrounded by trees.
Norumbega Inn. Norumbega Inn

Where to stay: Steeped in vintage allure, every corner of the newly revitalized Norumbega Inn hums a lullaby of simpler times. This elegant retreat offers 11 individually styled rooms and suites, furnished common areas and a kitchen, fleshing out its traditional bones with modern design. However, it’s the preserved historic elements—original wooden millwork, iconic turret and a glass-front porch—that temper the inn’s contemporary side.

A wooden dock leading out into the water, a small boat near the shore and a green island in the distance.
Bar Harbor. Paul Jebara

Day Five: Bar Harbor

A mere two-hour drive from Camden lies the rugged beauty of Mount Desert Island, the gateway to Acadia National Park. Upon arrival, you’re faced with an enticing decision: Embark on a two-mile hike up North Ridge Trail, or opt for a scenic drive instead? Whatever you choose, you’re well on your way to exploring the 27-mile Loop Road that snakes through the park’s unspoiled wilderness. The day is yours to conquer: Climb lofty peaks or meander along the tranquil Bubble Trail. Feel the thunderous power of crashing waves at Thunder Hole or seek serenity with afternoon tea at Jordan Pond House. As you sip, reflect on the stillness of the nearby pond—a soothing counterpoint to the day’s thrilling escapades.

Lush green mountainsides, water at the horizon, blue skies and clouds overhead.
Acadia National Park. Paul Jebara

Rather skip the hike? No problem. Submerge yourself in underwater exploration with Diver Ed’s Dive-In Theater, guided by the eponymous marine ecologist. Or, if you prefer terra firma, take in a free movie at Agamont Park’s alfresco Seaside Cinema on summer Wednesdays through mid-August. Then, dive into the food scene. Savor a genuine taste of the locale with Atlantic Brewing’s eclectic beers like Blueberry Ale and Cadillac Mountain Stout, perfectly paired with their veggie-friendly delights. Nearby, Havana serves a combo of stellar Latin American-inspired dishes. Plan for an early night—an unforgettable sunrise view from the peak of Cadillac Mountain puts even early birds to shame. And don’t worry, you can drive.

pool and loungers
The Claremont. The Claremont

Where to stay: The Claremont Hotel in Southwest Harbor blends Maine’s rustic character with a touch of European flair. Whether it’s a snug cottage or a spacious home, you’ll find the right fit here. Recently spruced up, its striking white exterior is a sight for sore eyes amid leafy pines and the glistening bay beyond.

How to Plan an Epic Maine Road Trip: A Five-Day Travel Guide