Southern Maine, first stop: Portland
Courtesy Alexa Erickson
Maine is known for its superb summertime beauty. Everything is alive and thriving, from the people to the lobsters, so no wonder the state is nicknamed “Vacationland.” Start in Portland, Maine. (It’s just an hour flight from New York City, so you can rent a car and be on your way.) The state’s largest metropolis, Portland is set on a peninsula extending into Casco Bay.
Where to stay: Check into the trendy Press Hotel, an Autograph Collection Hotel, in the Old Port.
Where to eat: Cruise through the Old Port waterfront and stop at DiMillo’s for to-the-point dining with the best view of the bay. The staff isn’t friendly but forward, and with a motto that says, “We don’t cook complicated masterpieces, just good food from fresh ingredients,” you’ll understand. Get the fried scallops, you’ll thank us later.
What to do: Walk the cobblestone streets of the Old Port, take a brewery tour (Portland is considered a leader in the microbrew movement), and take a ferry to the Casco Bay Islands, a group of islands located off the coast of Portland, with each island having its own vibe, attractions and activities. These are the 11 best road trips for stunning fall foliage.
Southern Maine, second stop: Kennebunkport, Maine
Courtesy Alexa Erickson
From Portland, head south and take a quick stop to see the historic lighthouse on Cape Elizabeth. It’s Maine’s oldest lighthouse, and a sight to behold. Then head to Kennebunkport, where breathtaking views await. Quaint in stature, but grandiose in coastline and things to do, this adorable town has both a harbor and a river running through it. It’s also home to the Bush family summer home, a slew of trendy restaurants and shops, and various festivals and celebrations.
Where to stay: Cape Arundel Inn & Resort is by far the most gorgeous resort in Kennebunkport, and perhaps all of Southern Maine. It has old-timey charm but with subtly nuanced luxury throughout. Gazing at the ocean from the Adirondack chairs on the lawn or from the wrap-around porch will give you that simple Maine flair. Champagne and warm cookies on arrival, and decadent design features in the rooms, like marble bathroom floors and French doors that open out to a delicious view of the Atlantic, will make you feel special, to say the least.
Where to eat: Hands down, Ocean Restaurant. Located at the Cape Arundel Inn & Resort, the warm atmosphere isn’t overbearingly chic, while the food is unbearably good. The inventive ocean-inspired cuisine is brought to you by the superbly talented and friendly Chef Pierre Gignac. The Rock Crab Velouté, featuring peekytoe crab, lemongrass scented bisque, beech mushroom, snow peas, and sweet corn purée is mind-blowing.
What to do: Check out a beach cruiser for free at the inn, and ride it into the bustling town. The cruise itself is enough to take your breath away with ocean views to your left and old colonial mansions to your right. Lock it up and step aboard the Spirit of Massachusetts, an enormous sailboat docked in the river right in the center of town. Keep it simple and order a pound of steamers (that’s Maine speak for steamed clams, just in case you’re confused by the ambiguous word on the menu). These are the 10 best winter road trips for families.
Southern Maine, third stop: Ogunquit
Courtesy Alexa Erickson
From Kennebunkport, cruise down the coast, and settle into Ogunquit. This is one of Maine’s most popular small towns, oozing with color from the people to the architecture. The food is both elevated and rustic. The scenic coastal strolls are endless.
Where to stay: The Cliff House is a coastal dream come true. Situated on the edge of the Atlantic on the rocky coast of Southern Maine, it boasts panoramic views from just about everywhere, including your swanky, nautical-themed hotel room. The resort is located in Cape Neddick, which is just a few minutes from Ogunquit. The infinity pool and spacious hot tub overlook nothing but vast ocean, with the occasional lobster boat cruising close to shore.
Where to eat: The Front Porch, located in the heart of downtown Ogunquit village has excellent food and an inviting atmosphere. The sing-along piano bar will surely keep you entertained long after you’ve filled yourself to the brim with scrumptious bites like the blue cheese mussels, lobster flatbread, and the shrimp and scallop carbonara.
What to do: In the morning, stroll Marginal Way, a cliff walk with coastal views, benches, and a lighthouse. You must spend the day on Ogunquit Beach. It’s a long, sandy peninsula with grassy dunes that resides between the Atlantic Ocean and the Ogunquit River. Plop your stuff down on the riverside, jump in the water, and let the river’s fast current whip you out to the ocean side. Then, take a walk along the beach and catch one of the volleyball games. Be sure to catch a show at the Ogunquit Playhouse—one of the town’s cultural icons.