Bar Harbor/Acadia
Ahh Maine!

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Bar Harbor, Maine is the gateway to Acadia National Park, which has a lot to offer including hiking and paddle-boarding.

Ahh Maine!

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Mt. Katadhin seen in the distance in Millinocket, Maine.

Portland
Ahh Maine!

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The historic Portland Head Light in Cape Elizabeth near Portland, Maine.

Best Places to Visit in Maine: America’s Most Northeastern State

Welcome to Maine! The most Northeastern state of the United States is defined by jagged coastline, rolling mountains, heavily forested interior, and picturesque waterways. It is also recognized by its seafood cuisine, especially lobster and clams. Do you like the sound of amazing food, great scenery and a chance to visit one of the most expansive wilderness areas on the East Coast? Then buckle up, because this itinerary is full of some of the best places to visit in Maine!
Prepared By:

James Wynn

Adventurer & Photographer

Maine Itinerary

Start / End

Boston, Massachusetts

States Covered
National Parks

Acadia

Total Distance

1,800

Suggested Days

At least 14

Suggested Seasons

Spring, Summer, Fall

#ThisIsMyRoute

Overview

Do you like amazing food, amazing scenery and amazing East Coast wilderness? Then buckle up, because this itinerary is packed with the best places to visit in Maine. In this itinerary, you will fly into Boston’s Logan International Airport before heading up north to the coastal areas of Maine, with a stop at the only National Park in New England, Acadia. Once you get to the very tip of eastern Maine, you will head west into the vast forested interior of Northern Appalachia. Don’t less the unfiltered destinations on this itinerary fool you. The cities and communities you’ll pass through have a vibrant and progressive feel to them, with world-class shopping and dining and an eclectic locale that will be the highlight of this amazing trip.

Preparation

We recommend approximately 14 days for this trip in order to experience each town and activity without feeling too rushed. This itinerary is full of suggestions of some of the best places to visit in Maine, with overnight stops in towns along the way. Plan your trip accordingly so that you experience places that spark your interest the most. These areas can be crowded in the summertime due to events and beautiful weather. Wintertime is still beautiful; however, many roads are closed and you cannot drive into some of the higher elevations. The majority of this trip will be relatively short drives between stops. Though this itinerary is a day-to-day guide, it is only a guide. Feel free to customize your schedule, taking as much time as you need to fully experience all that Maine has to offer.

Itinerary

LAND IN BOSTON, DRIVE TO YORK

Best Places to Visit in Maine

1 HOURS/60 MILES

To begin, arrive early in Boston and rent your car from the airport. Then, set out north toward your first stop in York. Situated beside the Atlantic Ocean on the Gulf of Maine, York is a well-known summer resort town. It is the perfect town to get prepared and excited to start your road trip. When you get into town head to the Dockside, a quintessential Maine bed and breakfast.

 

Best place to stretch your legs:
FISHERMAN’S WALK
Best place to learn about the area:
OLD YORK HISTORICAL SOCIETY
Can’t miss it:
YORK BEACH
Best photo op:
CAPE NEDDIK NUBBLE LIGHTHOUSE
Best place for cocktails:
WIGGLY BRIDGE DISTILLERY
Best place for Maine lobsters:
OFF THE BOAT LOBSTERS
THE ORIGINAL PORTLAND

50 MINUTES/46 MILES

Welcome to Portland, the East Coast Portland that is. Set on a peninsula extending into Casco Bay, Portland has a distinct, charming New England feel with a modern twist. The Old Port waterfront features working fishing wharves and converted warehouses with restaurants and shops. Nearby, the Western Promenade is a public park atop a bluff, offering river and mountain views. Its surrounding district, the West End, is full of Victorian-era homes, including the Victoria Mansion museum. With so much to discover, Portland is easily one of the best places to visit in Maine.

 
Best short hike:
WINNICK WOODS
Best way to see the city:
FROM A FIRE ENGINE
Most unique experience:
CATCH YOUR OWN LOBSTER
Best place to get some culture:
PORTLAND ART MUSEUM
Best place for a stroll:
CONGRESS STREET HISTORIC DISTRICT
Best place to eat oysters:
EVENTIDE OYSTER CO.
 
ROCKLAND

1.5 HOURS/77 MILES

Home to the Maine Lobster Festival, Rockland is spectacular coastal town. Considered a hidden gem and one of the best places to visit in Maine, the town was named “One of the Prettiest Small Towns in America” by Forbes Magazine. The area is home to a sprinkling of islands in and around Penobscot Bay. Take a sail around the area the get reacquainted with your land legs at Rock City Coffee.

Best walk:
HARBOR TRAIL
Best scenic drive: 
NORTH SHORE DRIVE TO OWL HEAD LIGHTHOUSE
Can’t miss it:
ROCKLAND HARBOR BREAKWATER
Best place for a stroll:
ROCKLAND MAIN STREET
Best place to learn about lighthouses:
MAINE LIGHTHOUSE MUSEUM
Best place for dinner:
ARCHER’S ON THE PIER
ACADIA NATIONAL PARK AND BAR HARBOR

2 HOURS/80 MILES

Next, follow Highway 1 to Bar Harbor, the gateway to Acadia National Park. Once you get to Bar Harbor, you are going to need some energy for your foray into Acadia. Grab breakfast at Jeannie’s Great Maine Breakfast then make your way into the park to explore the dramatic and rugged coastline. Stop at Rockefeller Welcome Center for helpful information about the park. Acadia National Park has lots of outdoor activities including hiking, climbing, and paddle-boarding. After you get back to Bar Harbor, get a room at the Acadia Hotel. There are a number of trendy restaurants in Bar Harbor serving up their own renditions of lobster, a regional favorite. Check out some nighttime entertainment at Reel Pizza Cinerama, a combination art-house movie theater and pizzeria. Lastly, grab a frosty pint at Leary’s Landing, the closet Irish Pub to Ireland in America.

Best way to see the park:
TAKE A RANGER LED PROGRAM
Can’t miss it:
BASS HARBOR LIGHT HOUSE
Best place to watch the sunrise:
OCEAN PATH TRAIL
Best place to hike:
PRECIPICE TRAIL
Best place for a dip:
SAND BEACH
Best photo point:
OTTER CLIFF
MACHIAS

1.5 HOURS/80 MILES

In Maine lexicon, Machias is known as a DownEaster Town, located in the eastern most point of the state. Known for its picturesque harbors dotted with fishing boats, meandering rivers, and historic sites pre-dating the Revolutionary War, Machias has another tasty little claim to fame: blueberries. Home to the Maine Wild Blueberry Company, the town holds the Machias Wild Blueberry Festival every year in August. Snag a room at the Riverside Inn for your stay in Machias, one of the best places to visit in Maine.

Best place for a hike:
MACHIAS RIVER PRESERVE
Can’t miss it:
BURNHAM TAVERN
Get out on the water:
SUNRISE CANOE AND KAYAK
Best place to take a bracing ocean swim:
ROQUE BLUFFS STATE PARK
Best place for a photo:
BAD LITTLE FALLS PARK
Best lobster roll in Maine:
HELEN’S
HOULTON AND THE COUNTY

2.5 HOURS/120 MILES

Houlton is the headquarters to boundless forests, mountains and rivers that make up Aroostock County, Maine. Known by several different names, including “The Last Frontier of the East” or just “The County” to local Mainers, Aroostock County is the largest county east of the Mississippi River. Head to Market Square in the town of Houlton. There you’ll find the commercial center of town which is listed on the register of National Historic Places. Get a room for the night at the Tall Timber Inn, a rustic Maine hideaway on the shores of Muduxnekeag Lake.

Best place to get outdoors:
DEBOULLIE STATE PRESERVE
Best place to learn about the Maine Acadian Culture:
ACADIA VILLAGE
Best museum:
NORTHERN MAINE MUSEUM OF SCIENCE
Best place to hike:
BANGOR AND AROOSTOOK TRAIL
Can’t miss it:
PLUTO AT THE HOULTON VISITOR’S CENTER
Best place for dinner:
THE COURTYARD CAFE
MT. KATAHDIN AT MILLINOCKET

1 HOURS/70 MILES

Millinocket is known as the “Biggest little City in Maine.” This port city is the northern terminus for trekkers on the Appalachian Trail and the gateway to Baxter State Park and Mt. Katadhin.  During the summer months, Millinocket teems with the energy of hikers and outdoor enthusiasts from around the world . The Shirlie House Bed and Breakfast is a particularly a charming place to rest your head.

 

Best place for wildlife:
DEBSCONEAG LAKES WILDERNESS AREA
Hike Katahdin:
THE KNIFE’S EDGE TRAIL
Can’t miss it:
THE WATERFALL TOUR
Best place to stock up on supplies:
KATAHDIN GENERAL STORE
Best place to shop:
WOODS AND WATERS SHOP
Can’t miss dinner:
RIVER DRIVERS
DOVER-FOXCRAFT

1 HOUR/50 MILES

Dover-Foxcraft is home to the Whoopie Pie Festival. That fact alone makes Dover-Foxcroft one of the best places to visit in Maine! It also sits at the entrance to the 100-Mile Wilderness, the final hard push for trekkers on the Appalachian Trail. We highly recommend getting a room for the night at Freedom House Bed and Breakfast on the Pistacaquis River.

Get outdoors:
PEAKS KENNY STATE PARK
Can’t miss it:
CENTER THEATRE
Best place to get some farm to table treats:
SPRUCE MILL FARM
Best photo op:
B52 CRASH SITE
Best way to see a moose:
MOOSE COUNTRY SAFARI AND ECO TOURS
Best place for dinner:
PAT’S PIZZA
GREENVILLE

1 HOUR/35 MILES

Greenville sits on the southern end of the largest lake in Maine, Moosehead Lake which stretches over 75,000 acres. Once you’re in Greenville, head for the Moosehead Lake Region Visitor’s Center for all the resources you need to make your stay memorable. Second, stop in to the Appalachian Mountain Club’s Little Lyford Lodge and Cabins. It’s not only a great place to stay, its a great way to meet people from all the world who have come to hike the Appalachian Trail. Finally, head to the Stress Free Moose Pub for dinner and drinks.

Can’t miss it:
KATAHDIN CRUISES
Best hike:
BURNT JACKET MOUNTAIN
Best place to stay:
THE GREENVILLE INN
Best museum:
MOOSEHEAD HISTORICAL SOCIETY
Best place to shop local:
DOWNTOWN GREENVILLE
Best Place to try a little local wine:
SPOTTED CAT WINERY
MADISON

1.5 HOURS/65 MILES

Madison is a river runner’s paradise. Located right on the banks of the mighty Kennebec River, as it stands now, it’s a hidden secret among kayakers, but that won’t last long. On your way into town make sure you stop by the Maine Maple Products to get all the sugar you desire. 

Can’t miss kayaking experience:
THE MADISON WAVE
Best place to catch some live music:
SOMERSET ABBEY
Best place to go for a hike:
BIGELOW PRESERVE
Buy some local produce:
NORTH STAR ORCHARDS
Best place for a stroll:
THE HISTORIC PINES TRAIL
Best place for dinner and a show:
THE LAKEWOOD INN
OXFORD COUNTY

 1.5 HOURS/65 MILES

Paris is the County Seat of Oxford County and the hub of what is know as the Oxford Hills area. Made up of West Paris, Paris and Norway, as well as Oxford  and a few other communities, the region is a beautiful example of everything that makes Maine so amazing.  We recommend making Paris/Norway your base of operations for exploration. From there, it’s up to you to decide where you want to go and what you want to see, but one stop that will help you on your way is the Oxford Hills Chamber of Commerce.

Best scenic drive:
ROUTE 26
Best museum:
PARIS HILL HISTORIC DISTRICT
Best hike:
STREAKED MOUNTAIN TRAILS
Best shopping experience:
THE VILLAGE GIFT BARN
Can’t miss it:
THE MCGLAUGHLIN GARDEN AND HOMESTEAD
Best place to find amazing food and craft beer:
XV VAULT AND PUB
LEWISTON

30 MINUTES /30 MILES

Today is a very short driving day, but that’s because we wanted to give you a little taste of city life after your sabbatical in the Great Northern Woods, and Lewiston is just the place to do it. The second largest city in Maine, Lewsiton is fast becoming a center of hipness and big city fun. But it is also a city of amazing architeture, highlighted by the exquisite Basillica of Saints Peter and Paul.  One stop you absolutely need to make is to the Museum L-A. Its has engaging and well-researched interactive exhibits that will give you a great understanding of the area.  One can’y miss experience is to get a room at the Inn at Angora. You can have a traditional room, or if you want…you can sleep in a haunted room that used to be a crypt!

Cant miss it:
THORNCRAG SANCTUARY
One of a kind experience:
ANDROSCOGGIN BALLOON RIDES
Best hike:
MOUNT APATITE
Best place for a stroll:
DOWNTOWN LEWISTON
Can’t miss it:
ANDROSCOGGIN RIVER GREAT FALLS RIVER WALK
Best place for dinner:
FISH BONES
PAHK YA CAH IN HAVAHD YAHD

2 HOURS/117 MILES

Having a little trouble with that title? It says, “Park Your Car in Harvard Yard,” in that classic South Boston Accent. Well, get your ears tuned and get ready for Boston. This is a world-class city and there are a million things to do here. A great place to start would be to head to Boston Commons and stop by the Visitor Center. Ditch the car at a garage in the North End and take “the T” (subway) around the city. The historic neighborhoods around Beacon Hill and Downtown are perfectly suited for walking and taking in the buildings, streets and parks that were integral to the founding of the United States. With so much history and iconic local characters, Boston is undoubtedly one of the best places to visit in Maine to top off your itinerary.

Best historic walk:
THE FREEDOM TRAIL
Can’t miss it:
WATCH THE SOX PLAY AT FENWAY PARK
Best place to view some art:
ISABELLA STEWART GARDNER MUSEUM
Best haunted place to stay:
THE OMNI HOUSE HOTEL
Must see district:
HARVARD SQUARE
Best place for dinner:
BEACON HILL DISTRICT, CHARLES STREET
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