If you like road trips, it’s no wonder you love Maine. Despite having pockets of population mixed with vast areas of wilderness, we’re actually a pretty great state to explore via road. Our beautiful nature makes themed trips to outdoor attractions easy and our lovely coast makes for a scenic way to spend a weekend. Today, we have another of our unique themed road trips in Maine for you, and get ready, because it’s one of the best! Rather than set your GPS for attractions, we’re taking you through some of the most picturesque small towns in Maine. You’ll love getting a sense for how different places live and we encourage you to stop along the way for tasty treats at some local spots. And, as always, we’ve mapped the entire trip for you on Google Maps. Let’s go!

Google Maps
Begin by fueling up at Coffee Roasters of the Kennebunks!
Coffee Roasters of the Kennebunks, 163 Port Rd, Kennebunk, ME 04043, USA
Coffee Roasters of the Kennebunks / Facebook
The Duckett family has created a perfect local coffee shop, complete with pastries and local crafts. Stop in before you head north to get yourself fueled up!
1. Kennebunkport
Kennebunkport, ME 04046, USA
Peter Bond / Flickr
You'll start your journey in one of the most beloved Maine tourist towns - Kennebunkport. Perfect for a visit in the summer, spring, fall and winter Kennebunkport is always beautiful. Start your trip by getting slightly out of town by heading to The Rachel Carson National Wildlife Refuge, which has a significant portion of lands in Kennebunkport northeast of Cape Porpoise and through Goose Rocks. This lovely little town is one of the most charming small towns in the country, in fact!
2. Bath
Bath, ME 04530, USA
Paul VanDerWerf / Flickr
Bath is renowned for its shipbuilding industry and has become known as the "city of ships." It's also one of the places you can visit to really experience Old Maine. The famous "Bath Iron Works" can still be found here. Stop by the Maine Maritime Museum as well as the Chocolate Church Arts Center which often hosts incredible community events.
3. Phippsburg
Phippsburg, ME 04562, USA
Ryan Taylor / Flickr
Sitting on the west side of the mouth of the Kennebec River, Phippsburg is a lovable small town with a tight community. There's no shortage of outdoors to enjoy here. You'll find the Bates-Morse Mountain Conservation Area, Fort Popham State Historic Site; along with Fort Baldwin which overlooks Fort Popham. Head over to Popham Beach State Park and Pond Island National Wildlife Refuge for even more of that lovely slow pace. The population here is about 2,200, so it's a wonderful place to experience some peace and quiet.
4. Port Clyde
Port Clyde, St George, ME 04860, USA
C Hanchey / Flickr
Port Clyde is the southernmost settlement on the St. George peninsula in central Maine. In the 19th century, Port Clyde became a busy port with granite quarries, tide mills for sawing timber, and shipbuilding and fish canning businesses. Today, the area's quiet location attracts artists and writers. One of its most notable attractions is the Marshall Point Lighthouse. You may remember it as one of the most beautiful scenes during Forrest Gump's cross-country run in the movie, "Forrest Gump." It's also a particularly lovely place to visit in the winter.

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5. Rockport
Rockport, ME, USA
smilla4 / Flickr
The town of Rockport is close to Camden, but many believe it has far more unspoiled character. Forbes Magazine even named it one of America's prettiest towns! Rockport is named for its rocky land and its limestone industry. If you have some extra time, you can jump on the ferry to Vinalhaven from here as well. It will take an overnight trip on the island to truly experience it. But, don't worry. You can jump right back on the road trip when you take the ferry back!
6. Belfast
Belfast, ME 04915, USA
smilla4 / Flickr
We can't talk about Belfast without also including the many small towns that surround it. This entire area represents some of the best of small-town Maine. It provides a great mix of art, local food and waterfront views. In June 2015, the first "Maine Fare" took place, celebrating and sharing local artisans, food and musicians. We think Belfast is the coolest town in New England!
7. Searsport
Searsport, ME, USA
Dave Hensley / Flickr
Searsport is Maine's second largest deep-water port and is ideally located from the point of view of railroad, wood products and other development interests. Searsport has a rich maritime history. During the 19th century, the port had 17 shipyards and built 200 ships. It is the second largest deep-water port in Maine and is ideally located at the confluence of the Penobscot River estuary and the Penobscot Bay. The rich heritage of the town can be seen at the Penobscot Marine Museum in town -- this is such a cool attraction that not enough people visit.
8. Castine
Castine, ME, USA
Roser Martínez / Flickr
Home to the Maine Maritime Academy, Castine has a rich seafaring history. At this stop on your road trip, check out the town's post office - the oldest continuously running one in the USA. Castine is a marvelous town to visit in the fall. when the leaves change!
9. Brooklin
Brooklin, ME 04616, USA
smilla4 / Flickr
Brooklin is named for the brook that separates it from Sedgwick, the town it was originally a part of. Historically, the town was a fishing and overall seafaring place. Fun fact: Allegedly, an 11th-century Norse coin was found in Brooklin. If this is true (some believe it to be a hoax), it would be the only physical evidence of Nordic settlers having entered the United States. An alternate explanation is that the coin was brought to the site not directly by Vikings, but rather through trading.
10. Stonington
Stonington, ME 04681, USA
jar [o] / Flickr
The lovely town of Stonington is located on the southern portion of Deer Isle. It was incorporated as a town in 1897 and renamed from Green's Landing to Stonington for its granite quarries. Despite its somewhat hard to reach location, you'll find plenty to enjoy here. From the Stonington Opera House to the museum, it's a lovely place to end your road trip and add on a few days to enjoy yourself.
What do you do after tackling the best road trips in Maine? Why, book yourself at the Pilgrim's Inn, that's what!
Pilgrim's Inn, 20 Main St, Deer Isle, ME 04627, USA
Pilgrim's Inn / Facebook
The Pilgrim's Inn, located in Deer Isle, overlooks Northwest Harbor and a small mill pond. It was built in 1793 and today also houses the Whale's Rib, where you'll definitely want to grab dinner!

Now that you’ve got the road trip wheels turning (see what we did there?!), you’re ready to check out some more of the best road trips in Maine. We have a waterfalls road trip, an abandoned places road trip, and even one for Maine’s lighthouses! Happy exploring!

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More to Explore

Best road trips in Maine

Sarah | July 31, 2021

What are the best road trips I can take in Maine?

Are you looking for the ultimate road trip adventure in the Pine Tree State? We’ve compiled the best road trips in Maine, and all are amazing adventures that belong on any Mainer’s bucket list. From exploring the state’s most scenic byways and charming towns, to enjoying the best of the fall foliage in the autumn, to exploring Maine’s creepiest locales (this is a fun one for the fall!), you’re bound to find an adventure on this list that really speaks to you!

What's the smallest town in Maine?

  • Beddington, a town in Washington County, is the smallest organized town in Maine. The population was 50 at the 2010 census, and at last check, this number had dwindled to just below 40. It's a lovely little place, however, and definitely worth visiting when you have a chance!

What's the most charming town in Maine?

While we adore all of Maine's small towns, it simply doesn't get more quintessentially East Coast than Kennebunkport. This unassuming beach town is all weather-worn boats and craggy coastlines, whitewashed homes, and unpretentious sea shacks. (The lobster rolls from The Clam Shack are particularly noteworthy, and really a must-try for any self-described foodie.) Kennebunkport has been lauded as one of the best places to live on the East Coast, and after visiting, you might just want to drop everything and move to this charming small town, too.

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