The Best Road Trip Getaways Outside of Portland Maine

Portland, Maine is having quite a moment. Over the past decade, it's transitioned from dreamy Northeastern hamlet to a mainstay in the national conversation, thanks to its stellar food scene, explosion of world-class breweries, and a distinct vibe that clashes small-town charm with maritime traditions and a desire to embrace the new. It's a place that's managing to change without losing sight of what it is, and that makes it one of the 20 places we're dreaming about in 2020.

But my home state of Maine is so much more than Portland and Stephen King references. It's a state whose tranquil towns, dense forests, towering mountains, and vast shorelines all but scream "road trip." Enjoy Portland, for sure, but use it as a springboard to hop around the state.

Head south and you almost immediately find picturesque beach towns straight out of an L.L. Bean catalog (probably because they are). Go north with sights set on Acadia National Park and explore the woodsy terrain and quaint villages along the way. Whichever direction you choose, here's the perfect three-day itinerary to help guide you on a safe, socially-distanced road trip along Maine's coast. Don't worry, you'll find plenty of lobster.

This three-day journey south doesn’t cover much mileage, but you’ll hit charming coastal towns and be thrust into the burgeoning food scenes popping up in Portland’s orbit. Avoiding some overpopulated locales, you’ll get the beachy oases you’re looking for without battling strangers for a six-foot-apart spot to lay your towel down.

You’re kicking off your trip in Portland, a city practically dripping in nautical character. If you’ve somehow avoided Maine’s famed lobster, there’s one place you have to stop before you get too far afield. Drive about 15 minutes south to Cape Elizabeth and you’ll run into the state’s quintessential postcard picture: Portland Head Light. Outside of the oldest lighthouse in Maine is Bite Into Maine, a food truck that serves hearty lobster rolls piled high with huge chunks of crustacean. Grab one Maine-style with light mayo and chives, then park yourself in Fort Williams Park overlooking the lighthouse for a picnic soundtracked by crashing waves.

You’ll have plenty of time to soak in rocky coastal views during this trip, but be sure to make a pitstop inland before hitting the sand, if only to score some candy for the trip. Small town Saco’s general store, The Way Way Store, will transport you back in time, serving old-school groceries that somehow still exist outside of postcards. Grab a Moxie and a bag of candies for the road, but budget time to hear some of the place’s long history.

Next, you will be tempted to go to Old Orchard Beach, but don’t. It’s a little quieter this year but it’s typically an absolute zoo, so sneak off to the tiny stretch of beach dubbed Biddeford Pool instead. Parking at Fortunes Rocks and Biddeford Pool Public Beach is limited and only a number of permits are available to locals and out-of-towners each season, but taking a short walk or bike ride will be worth it.

Much of Biddeford’s rapidly growing beverage scene is housed in giant brick buildings that formerly served as paper and textile mills on the edge of the Saco River. Visit Banded Brewing Co to stock up on brews for later or sip outside on their deck. Just don’t forget your mask. You can also opt for a different drink experience at the (mostly) natural wine bar, Lorne, where employees really know their stuff, or at Round Turn Distilling, where you can down their popular Bimini gin across the street. Both currently offer takeout and delivery.

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Before you head off to the next destination, I’d typically insist you grab one of 15 seats at Biddeford’s Palace Diner, but these days, you’re able to devour a sky-high tuna melt or hearty fried chicken sandwich outside without worrying about wearing half of it in front of an audience. The spot is a national sweetheart for a reason, so order a few things to share, and don’t leave without eating a stack of buttermilk flapjacks with a big scoop of whipped butter on top.

Drive 20 minutes through winding, wooded roads and you’ll reach Kennebunkport. But first, you’ll want to make a quick detour to drive by Walker’s Point. No, it’s not another one of Maine’s 65 lighthouses -- it’s the giant summer home (ahem, compound) of George H. W. Bush, regularly visited by his family. After pulling over to ogle at the giant home jutting out into the water and all the security, drive into Dock Square, where you can pop into adorable shops selling plenty of Maine souvenirs, tourmaline jewelry, and tote bags made from used ship sails.

Kennebunkport’s positioning as a tucked-away port makes it a calm place to get out on the water. Sailboats like the Pineapple Ketch and the Schooner Eleanor are still running two-hour trips during the day and at sunset with reduced capacity and COVID-19 prevention guidelines. But if you feel safer sticking with your pod, you can opt for a private charter. Both allow you to bring your own beer, wine, and snacks for the trip, so pack up your cooler and set sail. For overnight accommodations, go historic with the namesake Kennebunkport Inn or get swanky at White Barn Inn.

Another day, another 20-minute drive. The next stop is Ogunquit, a beach town that has fewer than 1,000 year-round residents, but comes alive in the summertime. This three-mile beach has all the amenities, including a nearby parking lot, food stands and souvenir shops -- and regular reminders to keep your distance and wear your mask. If you stake out a spot on the southern end of the beach, the changing tide creates a natural lazy river that will pull you around a jetty and into the ocean as it turns from high to low.

The beach town is surprisingly known for its nightlife, but the venues are somewhat unexpected. The Ogunquit Playhouse is one of the last remaining theaters from the “summer stock era” in the ‘20s when Broadway hopefuls would perform in coastal towns during the warmer months. The theater itself is closed this year, but you can still listen to Broadway alumni sing show tunes at Patio Cabaret events. 

For something a little more lively, the towns' gay bars are the place to be. The Front Porch typically hosts roaring piano singalongs at the bar upstairs, but right now, you can get your fill of piano tunes from the patio. Down the street at Maine Street, drag shows are still going on a few nights a week. From hundred-room resorts to tiny inns and cabins, there are dozens of beautiful accommodations to choose from when you're ready to turn in for the night.

Maine may be known for its jagged, rocky coast with tons of islands (more than 4,600, to be exact). But it’s not called the pine tree state for nothing. As you head north, you’ll snake through sleepy towns with historic homes from the 1800s and true mom-and-pop shops that don’t even make the map. When you reach your final destination you’ll be greeted by untouched forest and dozens of scenic hiking trails perfect for a socially-distanced getaway.

Whether you follow this itinerary word for word or scope out your own spots along the way, you’ll find opportunities to hike, bike, kayak, camp, and just get outside. So before you get too far from Portland, pull over in Freeport and stock up on essentials at an iconic Maine store. You may think it’s all bean boots, but L.L. Bean’s flagship store has just about everything you could need while in the state, whether it's a sweatshirt to shield you from the ocean breeze or camping materials for the more daring. You can pre-order for curbside pickup. A giant version of the store’s popular boots -- an admittedly strange roadside attraction -- sits outside, where may even see the bootmobile drive by.

Mainers will aggressively defend their rights to the whoopie pie -- a dessert featuring dense chocolate cake rounds with frosting sandwiched between them -- from Pennsylvanians who naively think the dessert is theirs. So pick up whoopie pies for everyone in tow at Wicked Whoopies before embarking on a 45-minute drive to Wiscasset. This small village is home to more than 30 antique stores, including Lilac Cottage Antiques and the Wiscasset Antiques Mall that you should take your time going through.

And finally, the spot that really put this town on the map: Red’s Eats. This place is a true lobster shack about the size of a minivan, and it’s no secret that they serve the best roll in the state. You’ll be glad you opted out of the pricey twin lobster dinner while you were in Maine’s big city, but be ready to wait in a line that stretches down the street.
MORE:Every old-school place to eat along Route 1, including Red's

Avoid falling into a food coma until you travel 45 minutes up the coast to Camden. There, you can spend the night in one of the many historic homes (think clawfoot tubs and sprawling gardens) that now house bed and breakfasts run by sweet locals, among them the Blackberry Inn.

Wake up in Camden (one of the best small towns in the country!). Stroll along the idyllic harbor, but first, get your bearings from the top of Mount Battie Trail. It’s an easy hike at just about a mile up and leaves you with unbeatable views of the harbor. You can take on a more adventurous climb at Camden Hills State Park later in the day, too.

For the evening, head downtown for an experience that feels frozen in time. Old homes, classic candy shops like Uncle Willy’s, and restaurants like 127-year-old Boynton-McKay Food Company set the scene for this traditional small town. If you want something more modern, check out lauded Long Grain or Natalie’s before heading to your final stop in Bar Harbor. For nature-lovers there are many campgrounds in the area, or opt for a room at a seaside resort.

First thing’s first, be the first in the country to see the sunrise. Head into Acadia National Parkbefore it’s bright and early and you can do just that at Cadillac Mountain, the highest point on the eastern seaboard. Grab your flashlight and hike two miles up North Ridge Trail to the summit or just drive and save your physical activity for later in the day -- there will be plenty of opportunities for that.

After a breakfast picnic atop the mountain (maybe a blueberry muffin?), return to the car and drive Loop Road. The main thoroughfare is 27 miles around the entire park, so it’s the perfect way to sample the area's natural beauty before choosing your adventure for the day. You’ll see plenty of people scaling the park’s major mountains if that’s your thing, but you can also hike the wide, smooth Bubble Trail for something easier.

Continue to explore by car and go see Thunder Hole, a rocky cavern that booms like thunder when the waves roll in, before settling down for popovers and afternoon tea overlooking a glassy pond on the lawn at the Jordan Pond House.

No matter what your day in Acadia National Park brought, you’ll deserve a break come late afternoon. So drive back to downtown Bar Harbor for dinner and dessert. This is your last day -- unless you do the southbound journey too, we’re not stopping you -- so make sure you’ve gotten all your Maine foods in.

Head to the grocery store to pick up W.A. Bean & Son signature red hot dogs for grilling, make sure you have had blueberry-something, and maybe even drink a Moxie -- actually scratch that, don’t let the state leave a bad taste in your mouth from its weird soda. It's an acquired taste maybe not worth acquiring. 

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