Maine Itinerary: USA’s Most Northeastern State

Maine Itinerary: USA’s Most Northeastern State

Ahh Maine! The 9th least populated state in the Unites States is defined by its jagged, rocky coastline; low, rolling mountains; heavily forested interior; and picturesque waterways, as well as its seafood cuisine, especially lobster and clams. Enjoy our maine Itinerary!


Prepared by:

maine, Massachusetts

Boston, Massachusetts

Total miles:

Suggested days: 
At least 14

scenic road trip

Recommended for: 
First-timers to the United States, honeymooners, photographers, road trippers, sea food lovers

Suggested season: 
spring, summer, fall


Do you like amazing food, amazing scenery and a chance to visit one of the most expansive wilderness areas on the East Coast? Then buckle up, because this Maine itinerary will have everything you are looking for. 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 and into the vast forested interior and the mountains of the Northern Appalachians. But is this overview leads you to believe that Maine is a tactless wilderness, you would be wrong. The cities and communities that we are sending you to have a vibrant and progressive feel to them, with world-class shopping and dining, and an eclectic locale that will be the highlight o this amazing trip.

How to Prepare

We recommend approximately 14 days for this trip in order to experience each town and activity without feeling too rushed. You have a lot of miles to cover, so we suggest spending at minimum a day at each stop.  This itinerary is full of suggestions of some of the best places to fully experience the area, with overnight stops in the towns along the way. Plan your trip accordingly so that you experience the places that spark your interest the most. These areas can be crowded in the summertime, and for good reason. There are multiple events and the weather is beautiful. Wintertime is still beautiful in these places, however, many roads are closed and you cannot drive into some of the higher elevations. In the northern parts of the state, winter is characterized by cold temperatures and lots of snow. Summertime temps in these places are characterized by warm days with lots of humidity, so take that into account as you decide your travel dates. The majority of this trip will be relatively short drives between stops, but this is to allow you the most time at all the amazing places that you have traveled so far to see. Though this itinerary is a day to day guide, it is only a guide and you should feel free to adapt it however you want, taking as much time as you need to fully experience this wonderful part of the world.

DAY 1: land in boston, drive to York

1 hours/60 miles

This is a shorter day for a good reason. We suggest arriving early into Boston and renting your car from the airport and setting out north toward your first stop, 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. The first thing we would recommend doing when you get into town, is to head to the Dockside. Its a quintessential Maine Bed and Breakfast and will give you the perfect introduction to this amazing place.

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 Lighthoue

Best place for cocktails:

Wiggly Bridge Distillery

Best place for Maine lobsters:

Off The Boat Lobsters

DAY 2: The Original Portland

Lighthouse on the coast of Maine.

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 New England feel to it, which it what gives it is charms, while being at once modern and pretty darn hip. 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.

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.

DAY 3: Rockland

1.5 hours/77 miles

Home to the Maine Lobster Festival, Rockland is great coastal town. Considered one of the hidden gems of the Maine Coast, the town was named “One of the Prettiest Small Towns in America” by Forbes Magazine. One thing the area is known for are the plenitude of islands in and around Penobscot Bay. One of the things we would highly recommend you fit into your schedule is to take a sail around the area. After that, you might need to re-find your land legs, so head to Rock City Coffee to re-energize.

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

DAY 4: Acadia National Park and Bar Harbor

acadia national park

2 hours/80 miles

Today you will be driving along the beautiful Highway 1 to your destination; 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. We would reccomend breakfast at Jeannie’s Great Maine Breakfast  Once you get breakfast make your way into the park to explore the dramatic and rugged coastline. The first stop you should make is to the Rockefeller Welcome Center. It will be a great guide to the park. After you get back to Bar Harbor we recommend getting a room at the Acadia Hotel. There are a number fine dining establishments in Bar Harbor – lobster is a regional specialty – and some nighttime entertainment, like Reel Pizza Cinerama, a combination art-house movie theater and pizzeria. Or try a more traditional establishment like Leary’s Landing, the closet Irish Pub to Ireland in America. Acadia National Park has a lot to offer including hiking, sight-seeing, and paddle-boarding.

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

DAY 5: Machias

1.5 hours/80 miles

In Maine lexicon, Machias is known as a DownEaster Town, located as it is, 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. One thing we would recommend doing in Machias, is getting a room at the Riverside Inn. Great place with a nice little seafood cafe attached.

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:


DAY 6: houlton and the county

2.5 hours/120 miles

Houlton is an outdoorsy kind of town, in that its is the headquarters to the boundless forests, mountains and rivers that make up Aroostock County. Aroostock County is the largest county east of the Mississippi. Known by several different names, including, “The Last Frontier of the East” or by many Mainers as just “The County,”  there are a number of small towns worth taking a short trip to see. The first thing we would recommend doing when you get into Houlton is to head to the Market Square. It is the commercial center of the town and listed on the register of National Historic Places. Get a room for the night at the Tall Timber Inn. Its a classic 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 for a hike:

Bangor and Aroostook Trail

Can’t miss it:

Pluto at the Houlton Visitor’s Center

Best place for dinner:

The Courtyard Cafe

DAY 7: Mt. Katahdin at Millinocket

1 hours/70 miles

Millinocket is known as the “Biggest little City in Maine” with good reason. It is a major supply point and the northern terminus for trekkers on the Appalachian Trail and the gateway to Baxter State Park and Mt. Katadhin.  During the summer months, Millinocket turns into an international town with hikers and outdoor enthusiasts flocking to the town, which gives it a really fun vibe. The first thing we would recommend is heading to The Young House Bed and Breakfast. It’s 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

DAY 8: dover-Foxcraft

1 hour/50 miles

Dover-Foxcraft is home to the Whoopie Pie Festival. Yup. Just let that sink in. You are headed to a town that holds a festival celebrating the Whoopie Pie. This should be your first clue that Dover-Foxcraft is a pretty fun town. It also sits at the entrance to the 100-Mile Wilderness, the final hard push for trekkers on the Appalachian Trail, before hitting Baxter and the northern terminus. We would highly recommend getting a room for the night at Freedom House Bed and Breakfast. It sits right 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

DAY 9: Greenville

1 hour/35 miles

Greenville sits on the southern end of the largest lake in Maine, Moosehead Lake. At over 75,000 acres, this  lake is HUGE, and Greenville is just the place to explore it from. The first stop we recommend is to the Moosehead Lake Region Visitor’s Center. They are going to have all the resources you need to make your stay spectacular. The second stop we would recommend is 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 AT. Speaking of which, 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

DAY 10: 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. After your sugar rush helps your drive into town, head to the Colony House Inn. It’s a classic Maine Bed and Breakfast.

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

DAY 11: 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

DAY 12: 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

DAYs 13 And 14: Pahk Ya Cah In Havahd Yahd

Boston skyline

2 hours/117 miles

Having a little touble with that tiltle? 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 so here, so a great place to start would be to head to Boston Commons and head to the Visitor Center. Driving around the city can be difficult for visitors, so one smart option would be to park 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.

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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