Best Places to Visit in Maine: America’s Most Northeastern State
Adventurer & Photographer
Road Trip Through the Best Places to Visit in Maine
Start / End
At least 14
Spring, Summer, Fall
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.
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.
LAND IN BOSTON, DRIVE TO YORK
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.
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.
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.
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.
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 Machias River Inn for your stay in Machias, one of the best places to visit in Maine.
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.
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.
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.
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.
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.
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!
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.