Top Fall Road Trips: Coastal Maine
Every season in Maine is spectacular, but there’s something extra special about fall. Between the brilliant cascade of foliage colors, the crisp temperatures that beg for a cozy sweater (a wool, cable-knit one if you want to look the part), and the way the coast settles into a calmer pace after the summer folk head home, there’s no better time to take a road trip through Maine. We’ve rounded up a few of our favorite stops along Maine’s rocky seacoast to stop and soak up before the snow begins to fly.
Coastal Maine Road Trip Leg One: Portland to Rockport
Most travelers arrive in Maine from points south, so it’s a fair bet Portland is a good first stop – and one of the last big cities before entering Maine’s more rural Midcoast region. As you wind your way up the coast toward Rockport, home of the Samoset Resort, you’ll be treated to coastal fishing villages, stunning vistas, and just the right amount of roadside kitsch.
Portland Museum of Art [Portland, ME]
Among the other priceless works of art by Andy Warhol, Winslow Homer, and Claude Money at Portland Museum of Art, you can see the brilliant, multi-colored 13-by-34 foot masterpiece, A Midsummer Night’s Dream, a permanent installation by Maine native Tim Rollins, which was inspired by the quilters of Maine and brought to life through his artists’ collective, Kids of Survival.
L.L. Bean [Freeport, ME]
Located just north of Portland, L.L. Bean is more than a Maine institution; it’s a way of life. From its lenient return policy – as in, if you’re not 100 percent satisfied, they’ll take back the item within a year of purchase – to its signature “Bean Boots,” you’ll love more than just the items for sale at this Maine retail legend. Fall is a great time to visit when Freeport’s summer crowds have thinned in this downtown built around its outlet shopping.
Red’s Eats [Wiscasset, ME]
Fondly known as “the prettiest village in Maine” found shortly after starting your journey north onto coastal Route 1, Wiscasset is home to Red’s Eats, an unassuming but oh so essential street corner shack. The line that winds down the sidewalk may tip you off, but beneath the humble exterior of this seafood joint lies a perennial favorite among locals and tourists alike. Proof positive: Red’s headlines the list of Samoset Executive Chef Tim Pierce’s top lobster rolls. Red’s rendition comes on a butter-toasted hot dog roll far too small to contain the entire lobster’s worth of meat that comes with it. Mayo and butter are served on the side, and you won’t find a speck of lettuce or celery anywhere within – Red’s Eats is where purists go to order a lobster roll.
Wildings [Damariscotta, ME]
No road trip is complete without a few keepsake souvenirs. For a fresh take on your run-of-mill Maine tchotchkes, head to Damariscotta’s Main Street to check out this
bright and airy lifestyle boutique. Newly opened in summer of 2021, the modern and minimalist space is chockfull of air plants, terrariums, driftwood, vintage bottles, and other locally made goods, like candles and pottery, that will liven up any living space.
Moody’s Diner [Waldoboro, ME]
You may have had lunch earlier in your trip, but by the time you make your way up Route 1 to Waldoboro, you’ll be ready for a quick stop to stretch your legs and eat a snack. At one of Maine’s most legendary classic diners, it will be hard to narrow down your choices. Moody’s Diner is famous for both its whoopie pies and the daily selection of a dozen or so homemade pies. There’s really no way to go wrong at Moody’s – aside from passing it by.
Where to Stay: Samoset Resort [Rockland, ME]
Regularly ranked among the best golf resorts in the US by Conde Nast Traveler, the Samoset Resort is perched on 230 waterfront acres that overlook Penobscot Bay in Maine. You might never leave the resort’s own peninsula, but you would miss out on the string of quaint communities of Rockport, Rockland, and Camden, known as iconic fishing villages with great art and culinary scenes.
Coastal Maine Road Trip Leg Two: Rockport to Bar Harbor
Refreshed from your evening ensconced at the Samoset, it’s time to continue on your way north. On the way to Mount Desert (pronounce it like “dessert” if you want to blend in with the locals) and Bar Harbor, acquaint yourself with a few coastal highlights. Upon your arrival in Bar Harbor, imagine yourself rubbing shoulders with Carnegies, Pulitzers, and other illustrious families from the Gilded Age, who used to frequent the area.
Rockland Breakwater [Rockland, ME]
Before you leave the Samoset’s grounds, make your way to the Rockland Breakwater for the nearly mile-long walk across the mammoth granite blocks that traverse Rockland Harbor out to the Rockland Breakwater Lighthouse. At the end of your walk, enjoy stunning 360-degree views of the harbor, explore the lighthouse, and catch a peek of Owl’s Head Lighthouse, too. When the fall foliage colors are out, this is a coastal scene that no postcard can capture.
Zoot Coffee [Camden, ME]
After your walk down the breakwater, make a quick stop at the locals’ favorite coffeehouse, Zoot Coffee in downtown Camden. This modern yet comfortable café has coffee and espresso as good as you’ll find in any big city, as well as simple, delicious food and baked goods. A freshly baked muffin and a hot cuppa are just what you need to continue your drive.
Penobscot Narrows Bridge & Observatory [Prospect, ME]
Taller than the Statue of Liberty and home to the world’s tallest bridge observatory, the Penobscot Narrows Bridge offers spectacular 360-degree views for those brave enough to climb to the top of the 420-foot-tall western tower. Hike to the top to take in the spectacular view of the foliage, then make your way down for a picnic at the nearby pavilion before a tour through Fort Knox, Maine’s largest and best-preserved military fortification.
Cadillac Mountain [Mount Desert Island, ME]
Before winding down your Maine road trip in Bar Harbor, there’s just one more stretch of road you must travel. The narrow, three-and-a-half-mile road that climbs up Acadia National Park’s 1,530-foot tall Cadillac Mountain will lead you to one of Maine’s most spectacular viewpoints. From the rocky summit of the mountain, visitors can see Bar Harbor, the Porcupine Islands, and Frenchman Bay – and on clear days, all the way over to New Hampshire’s Mount Washington, the highest peak in the northeast. Purchase a vehicle reservation pass at online for $6 and make your way above the tree line and into the clouds.
Where to Stay: Harborside Hotel & West Street Hotel [Bar Harbor, ME]
The Harborside Hotel, Spa & Marina, nestled in Bar Harbor’s picturesque waterfront, embodies the elegant history of “summering” in Maine, but still may be the best spot to enjoy autumn in town. The hotel can be found where Frenchman Bay meets downtown, where you can watch some seemingly too-big cruise boats navigate the bay this time of year from your much-more-comfortable quarters and waterfront balcony. The Harborside provides two-step access to all of downtown, plus the adjacent Bar Harbor Club. Built in 1929 by J.P. Morgan and once a private playground for Bar Harbor’s wealthiest summer residents, the club was recently restored to its former grandeur with the pool, tennis courts, and spa available for hotel guests.
West Street Hotel is just 300 feet away, around the corner on its namesake street. In Bar Harbor’s former life as the summer home of families like the Rockefellers, Vanderbilts, and Fords, West Street was where famous mansions and estates (then called “cottages”) were built. Today, the hotel is town’s only luxury boutique hotel, featuring modern design, magnificent ocean views, and one truly breathtaking rooftop pool. Hotel guests also have access to the Bar Harbor Club and its pool and hot tub around the corner during their stay.
