Get Lost in Maine

Few things are more iconic than a late summer trip to Maine. Miles of dramatic coast, postcard-perfect lighthouses, and corner lobster stands are just some of the reasons why millions of people throng there each year. Small wonder the state has earned the much-deserved moniker “Vacationland.”

Finding the best beaches, patio dining, and quaint Main Streets you need for an awesome getaway doesn’t take much effort. But if you’re looking for a trip with a little more adventure and a lot less congestion, you’re going to have to get off the beaten path—and that takes a whole lot of insider knowhow. Luckily, we’ve got you covered: whether you’re looking for remote hikes or killer rapids, these trips will make sure you get lost in all the best ways.

1. Bomb with the Locals

Portland, Maine, is one of the hippest cities around, with coffee shops and record stores to spare. It also has a surprising number of killer mountain biking trails, all within an easy drive of city center. Shred the gnarl at Evergreen Cemetery, located on Stevens Avenue near the University of New England. With more than 239 acres to explore, the cemetery offers something for everyone, but is known for its hidden (and seriously technical) single-track: roots, rocks, heart-stopping drops, and natural jump features make it a favorite among local cyclists.

Just one town over, Falmouth’s Blackstrap Hill Preserve has enough steeps and twists to make sure you make good use of all your gears, along with stream crossings and wooden bog bridges to feed your stoke.

Once you’re warmed up, head over to Bradbury Mountain State Park. The park boasts 18 miles of trails designed by mountain bikers for mountain bikers. There you’ll find some several beginner rides, including some gorgeous loops through softwood forests. But what the park is known for is its advanced terrain: the O Trail will send you hopping through rock gardens and rocking fast hairpin turns, while the Switchback Trail will have your brakes screaming down a 200-foot drop. Whichever route you choose, don’t forget to save enough time to savor the view from the mountain summit.

Teching Out: All Speed Cycle and Snow can get your bike tuned up for any ride, then disassemble it and ship it back home for you, too. They also offer shop rides on Tuesday and Thursday evenings, which is a great way to see the area and get the down-low on other secret spots. Don’t want to bring your own machine? No problem. Gorham Bike & Ski rents bikes by the hour or the day, and its rental packages include a helmet and lock, too.

Best Recovery: If you’re at Bradbury Mountain, stop by Edna & Lucy’s, the favorite eatery of the Trail Monsters, Portland’s trail running club. Members swear by the café’s homemade donuts and chocolate chili, but you can’t go wrong with a gianormous Reuben or grilled eggplant sandwich either. Once you’re refueled, swing by Sebago Brewing for a tour and tasting. Still not quite recovered? Head back into Portland and check out Soakology, a sanctuary for feet that offers a full menu of luxurious foot soaks, massages, and reflexology in a spa that looks like it was pulled straight out of Marrakech, then head to Nosh Kitchen Bar for some bacon-dusted french fries and a side of fried pork belly. You’re welcome.

2. Paddle Like You Mean It

You might feel like you’re on the edge of the Earth when you get north of Bangor, and for good reason: the northern half of the state is largely unincorporated and is designated only by township and range. Comprised primarily of Aroostook County, the area is known as “the county” by locals and boasts some of the best untrammeled wilderness experiences around.

The crown jewel of the region is the Allagash Wilderness Waterway, a 92-mile stretch of pristine lakes, rivers, and streams. With only a few outlets and no permanent residents along the river corridor, it’s about as removed as you can get, and offers some of the best paddling you’ll find.

Tackling the entire waterway will take about 10 days and some careful provisioning. Don’t have that much time? Consider a three- or four-day trip instead. Several sections are solely flat water, but most visitors really groove on the class I and II rapids located on the lower Allagash. No matter the trip, you’re all but guaranteed to see some of the local wildlife, including loons and moose, and the trout fishing can be tremendous, particularly as the days get cooler.

Looking for a high adrenaline experience? Go head-to-head with the Penobscot River, the steepest river in the state. Put in at McKay Station if you want to brave Ripogenus Gorge, a class IV-V section of punishing whitewater. Keep going if you want to try your luck at the Cribworks, some of the most challenging paddling in all of New England. Neither is for the faint of heart, and even experienced paddlers may want to hire a guide to help them scout the best line.

Outfit yourself: From canoes and kayaks to tents and cookware, Katahdin Outfitters can trick you out for any Allagash trip. They’ll even shuttle your car from put-in to take-out to make your adventure hassle free. Pangburn’s IGA in Millinocket is a great place to provision: for a small fee, they’ll even pack up your food and have it waiting when you arrive. Penobscot Adventures will rent you an inflatable kayak or all the gear you need to try riverboarding (think boogie boarding on steroids); they also offer private and group guiding services. Northern Outdoors is one of the few guiding companies that regularly runs the entire Penobscot, and each trip includes a grilled lunch with logging-camp portions of steak and salmon to keep you feeling fat and happy.

Post-Paddle Grub: Head to New England Outdoor Center, just a few miles from the Penobscot River takeout. The facility offers both tent camping and cabins for rent by the night, but the real reason to visit is River Driver’s Restaurant, where you can order anything from lobster macaroni and cheese to their signature burger. If you happen to be in the neighborhood on a Friday night, be sure to stop by for one of their famous fish fries featuring local Maine catch. Wash it all down with one of the five microbrews on tap (we recommend Allagash White to commemorate your adventure).

3. Build Your Own Beta

Maine has dozens of fantastic climbing spots, but none are quite as stunning as the routes on Mount Desert Island.

Also home to Acadia National Park, the island gets plenty of summer traffic, thanks to the park’s famous carriage trails and Bar Harbor’s shopping district, two reasons locals steer clear this time of year. You can get your dose of MDI adventure without the tourists trappings, though, simply by going vertical.

The island’s legendary pink granite has been a consistent favorite among climbers worldwide for one simple reason: it’s a wicked good time. You’ll find plenty of cracks and arêtes on the south wall of Champlain Mountain, one of the island’s major peaks. Otter Cliffs, located on the east side of the island, has earned an international reputation as one of the highest (and most stunning) coastal headlands in North America. Its 110-foot face rises directly out of the crashing surf and offers unparalleled views, and the nearly 40 routes there include both led and top-rope climbs for all abilities.

Reach the cliffs by a short hike in from the park’s loop trail, then rappel down to the cliff base to begin your adventure. The adjacent South Otter Cliffs offers similar views but easier terrain that will feel much more accessible to beginners and families. 

Gear Up: For the best in one-stop climbing prep, head over to Acadia Mountain Guides Climbing School, with locations in Bar Harbor and Orono. The staff there are all professional and veteran climbers, and they offer a range of guiding packages for novices and experts alike. Choose from a half-day experience on MDI or a multi-day exploration of some of Maine’s best alpine climbs. They also offer special packages for families of all abilities. Both locations include full service stores that rent gear and sell everything from gear to apparel. Wander into Cadillac Mountain Sports for a wide selection of best selling climbing brands, along with tents, packs, boards and more.

Check out: If the pitches on MDI haven’t provided enough solitude, hop the mailboat and head over to the Cranberry Isles. A one-day ticket will let you jump from island to island for no extra fee, and there’s plenty to see and do on each, from the Historical Museum on Little Cranberry to geocaching on Big Cranberry. On your way home, take Route 1 south and stop by the Narrows Bridge, which lays claim to the tallest bridge observatory in the world, then swing by Staples Homestead and rake your own organic blueberries. The farm has some of the most beautiful views in coastal Maine, along with plenty of old world charm, complimentary recipe books, and a winnower that’ll clean your berries and leave you grinning like a kid.

4. Make Tracks

Maine is the northern terminus of the Appalachian Trail and also the home of the Hundred Mile Wilderness, considered by many to be one of the Trail’s most challenging sections: encased in 15 million acres of wilderness, it’s some of the most remote hiking you’ll find in the country, and offers a variety of formidable terrain, from slate canyons and mountains to swift river crossings and waterfall drops.

It’s a trek absolutely worth undertaking, but one that can take more time (about 10 days, on average) and planning than most vacationers have. If you’re looking for all the beauty and less of the commitment, head over to Gulf Hagas, also known as the Grand Canyon of the East. Part of the Appalachian Trail corridor and managed by the National Park Service, the 2-mile long gorge was formed by the west branch of the Pleasant River.

The surrounding area includes remnants of Katahdin Iron Works, which produced thousands of tons of pig iron annually during the nineteenth century. Remnants of the blast furnace and charcoal kiln still remain, and plenty of interpretive signage makes a self-guided tour easy. Beyond it lies the Gulf Hagas Rim trail, a challenging nine-mile hike that will have you forging streams, scrambling over boulders, and pausing every few minutes to take in the awesomeness of the scenery.

The trail winds through the Hermitage, one of the only old growth pine stands left in the Eastern United States, and past Screw Auger Falls, a collection of six waterfalls that plunge from pool to pool, creating spectacular horsetail plumes as they do. Screw Auger can get crowded during the height of summer, so keep hiking if you’re looking for more solitude: Buttermilk and Stair Case Falls offer all the splendor and a lot less foot traffic, as well as emerald-green pools perfect for taking a quick dip.

Set Up Camp: Gulf Hagas is located just south of Millinocket and about 45 minutes east of Greenville. Decent car camping is available at Jo-Mary, or kick it up a notch and stay in one of the Appalachian Mountain Club’s lodges or cabins at Gorman Chairback. Looking for backwoods luxury? Consider renting a room in nearby Greenville. The lovely town at the base of Moosehead Lake has plenty of charming inns, including the very stately Blair Hill.

Embrace Old Time Luxury: While you’re in Greenville, hop aboard Kate, a 1914 Katahdin Steamship that takes guests on three-hour tours of the lake. Its galley turns out a mean cup of haddock chowder, and guests are welcome to bring their own alcoholic beverages. If staying landlocked is more your thing, T up for nine holes at picturesque Mount Kineo, New England’s second oldest golf course.

5. Haul Sail

Maine’s coast was once dominated by schooners—sleek tall-masted ships that defined the fishing and cargo trade for centuries. Most of the wooden vessels are long gone, but you’ll still find an active fleet of eight cruisers in the Maine Windjammer Association. Each vessel has its own personality, but they all make the most of Maine’s unparalleled sailing grounds: rather than maintain set itineraries, the windjammers follow the best winds by day and anchor in protected lees each night.

This is otherwise inaccessible landscape, and you’ll be hard pressed to find much evidence of contemporary development. Start each morning off with a plunge off the bow, spend your afternoons crewing and learning to read charts, or just check out on the foredeck. Each cruise includes a traditional Maine lobster bake, often on an uninhabited island, and there’s plenty of time for shore visits if you want to sneak in a jog or hike.

Sign On: The Maine Windjammer Fleet is based on the state’s midcoast, and most of the vessels depart from the towns of Rockland and Camden. Hop aboard the ketch Angelique for a weeklong yoga cruise, or go exploring on one of the vessel’s wooden stand-up paddleboards, handcrafted by Captain Dennis (who also shapes a mean surfboard and loves to talk waves). The Stephen Taber offers special wine tasting cruises, along with farm-to-table dining. The schooner Isaac Evans, which is also kid-friendly, does special astronomy cruises timed with meteor showers. With nothing but gentle seas around you, that makes for some pretty unparalleled stargazing.

Get Your Hands Dirty: Midcoast Maine is a real mecca for the local and slow food movements. MOFGA, the Maine Organic Farmers and Gardeners Association is just a short drive inland and regularly offers hands-on courses, along with farm tours and tastings. Saltwater Farm offers recreational cooking classes on their working farm, which overlooks the Penobscot Bay, and their café has some of the best alfresco dining around. If grazing is more your thing, stop by the Camden or Belfast farmers markets, where you can sample artisanal cheese, buy handmade sausages and salamis, and groove out with some very attractive barefoot locals.