A Comprehensive Maine Road Trip Itinerary

A Comprehensive Maine Road Trip Itinerary

If you are looking to explore the East Coast on a road trip, you should seriously consider exploring Maine! If you enjoy sightseeing by the ocean, you will love taking a trip through Maine since it has the longest coastline of any state in the United States. 

Furthermore, you will find every quant New England experience in Maine. You can explore coastal towns and sandy beaches, drive through tree tunnels, eat a lobster roll, and take trips to the beach. 

There are so many experiences to explore in Maine, and it can feel overwhelming to try and pack everything into one trip. Feel free to skip any of our recommended spots and keep driving. Similarly, you can start later or end earlier than what we have laid out.

Pick a series of stops that fit your interests and schedule! Make it a DownEast day trip or rest at Maine’s stunning campgrounds: the best road trips are the ones personal to you.

Keep reading to get all the information you need on a beautiful, memorable getaway through Maine. 

Before You Start

There are definitely a few things to consider before jumping in a car and starting a road trip:

Car Safety

First and foremost, figure out what car you will be taking and make sure it’s working properly. If you are driving your own car, check the tires, test your lights, test your brakes, and clean it out. Depending on the time of year, you might need snow tires or other safety equipment. 

You will also want to prepare for the long stretches of driving in between destinations. If you are traveling with someone else, have a conversation about how you will split up the driving. It’s important that you try to avoid one person driving for long stretches to avoid any accidents due to a tired driver. 

If You Don’t Live Near Maine

If you don’t live within driving distance of Maine, no need to worry! The Portland International Jetport is within a one-hour drive from New York, and they have flights coming from and going all over the USA. Roadtrippers head to Maine from Boston, Canada, New Hampshire, and more.

There is also a car rental service right at the airport, so once you land, you can grab a car, have it checked by the workers, and start on your journey.

Plan Some Entertainment

No matter how exciting your road trip is, the long hours in the car can get a little tedious. HearHere helps you make the most of your time on the road with bite-sized stories to help you get to know the world around you.

HearHere is a location-based audio platform that shares stories about the people, places, and history of the land they are traveling through. This will allow you to learn about the landscape you are driving through during your road trip, making every space you pass through even more exciting. 

HearHere connects generations by bringing the landscape to life through sharing stories that surprise, inform, and delight the listener. 

If you’d like to discover the history and related stories about the highways, cities, towns, and species you are driving through, sign up to gain access to thousands of bite-sized, location-based audio clips through your account

York / Cape Neddick

Now that you and your car are ready, it’s time for a scenic drive up to York for the first stop on your road trip bucket list.

As you drive into the area, stop and admire the Nubble Lighthouse. It gives a charming look at the fishing history that is the foundation for so many coastal towns. 

Then, head over to Long Sands Beach to soak up some sun and enjoy the Atlantic ocean breeze. This family-friendly beach isn’t usually too crowded, so it should make for a beautiful, relaxing first stop on your road trip. 

After spending a few hours at the beach, you might be ready to move around. We recommend hiking on Mount Agamenticus. There is only one hiking trail, and it’s fairly short, but it offers views of both mountains and the coast of Maine. 

This area also has many small, charming shops. You can browse antiques, quilts, clothes, and souvenirs. 

Ogunquit

After only a 15-minute drive down the coast, you will hit Ogunquit. 

If you are starting your day in Ogunquit, head over to the Cove Cafe. This charming breakfast restaurant is located in a classic Cape Cod-style house. It serves breakfast from 7 am to 11 am every day, and it will give you a charming breakfast experience that you could only get in a beach town on the East Coast. 

Afterward, you could head to the Ogunquit Museum of American Art. This museum has thousands of pieces of art and emphasizes American art. 

Once you finish at the art gallery, take a sunset cruise with Finestkind Scenic Cruises. This will give you a gorgeous view of the Maine coast from the water. While you are on the boat, a guide will discuss the lobstering industry and point out important landmarks. 

Finally, to end the day, check out the Ogunquit Playhouse. This playhouse opened in 1933, and it is actually listed on the National Register of Historic Places. Every summer, from May to October, they put on a series of musicals and plays that perform from Tuesday-Sunday each week. If there is a show on the night you are in Ogunquit, we highly recommend catching a performance.

Before or after the play, you can visit any of Ogunquit’s delicious restaurants. The Cornerstone Artisanal Pizza & Craft Beer is a hip restaurant that provides a warm atmosphere. While you are here, choose from the long list of artisanal pizzas and any of the local craft beers from nearby breweries.  

Kennebunkport

Located 20 minutes up the coast from Ogunquit, you will find Kennebunkport. To start the day, check out the restaurant, All Day Breakfast. Remaining true to its name, you can get breakfast here at any time of the day. So if you are driving to Kennebunkport in the morning, you don’t have to worry about missing breakfast hours. 

After taking a day off of the beach in Ogunquit, you might be ready to get your feet back in the sand, so check out Gooch’s Beach. This is a large beach with soft sand and plenty of space for you and your travel companions. There are also lifeguards at this beach, so you can feel safe going out into the water. 

After sitting at the beach all afternoon, take a stroll down Parsons Way Trail. This trail is two miles long and walks along the coastline, giving it incredible ocean views. There are benches along the way, which allow you to sit and soak up the view for a few minutes. Fun fact: the end of the trail will put you in front of President Bush’s summer house. 

After taking a walk, indulge in some local specialties at Nunan's Lobster Hut. You will be seated at a picnic table with a plastic bag as you eat lobster, lobster rolls, clam chowder, etc. 

Portland

Just a 35 minute drive away from Kennebunkport is Portland. 

The first sight to see here is the Portland Head Light. This lighthouse is still fully functioning, and it overlooks the Gulf of Maine. After you take in the sights of the lighthouse, head over to the Portland Arts District.

This area is condensed into a few blocks but has museums, galleries, theaters, and public art installations. Additionally, they host the First Friday Art Walk, which keeps the art institutes open later (5 pm - 8 pm) on the first Friday of every month. Many places will offer free admission or drinks to the guests of the First Friday Art Walk. 

If you have some extra time in the afternoon, check out the International Cryptozoology Museum. This is the only museum in the world that is exclusively used to explore mythical creatures like Bigfoot and Sasquatch. It is extremely entertaining and totally unique to Portland, ME.

After a day looking at art and Bigfoot prints, head over to Commercial Street. This street runs along the bay and is full of shops, pubs, and restaurants. While you wander in and out of shops or pubs, you can usually watch fishermen hauling their load from the day. 

If you are itching to see another show, you can look at the lineup at Merrill Auditorium. This auditorium hosts concerts, theater productions, and ballets. Additionally, it’s breathtakingly beautiful, so going just to admire its architecture is worth the trip alone. 

Some great restaurants to check out in Portland are Tandem Coffee for breakfast and the Red Sea for dinner. 

Bailey Island

Roughly a one-hour drive from Portland is Bailey Island!

Bailey Island holds 216 miles of coastline and contains multiple small islands. It is a small community, but travel to Bailey Island increases during the summer due to its beaches and beautiful scenery.

If you are ready to get back to the beach, head over to Mackerel and Garrison Coves. Not only are there public beaches here, but they also serve as a starting spot for working fishermen.

This means you can watch fishermen sail off in their boats while you relax on the beach. If these beaches are busy, you can head over to Land’s End Cove. Here, you can swim in the water and, if the conditions are right, try out surfing. 

If you are still trying to find the perfect Maine souvenir, you should go to Seaside Creations or Land’s End Gift Shop. This shop has countless treasures made by local artists that are a perfect way to remember Maine. 

After spending the day at the beach and in local shops, you can book an excursion on the water during sunset. Through Tevake Sailing Charters, you can take a trip along the coast in a sailboat. You will be with a sailing professional, so you don’t have to worry about safety, and it is a beautiful way to experience the sights of the islands. 

Damariscotta

After driving an hour out of Bailey Island, you will hit Damariscotta. 

For breakfast, head over to Barn Door Baking Co. Everything made here is made from scratch in the bakery. To pair with your breakfast, you can get a freshly ground espresso or tea. 

After having a nice breakfast, you will want to have a leisurely day exploring all of the shops that Damariscotta has to offer. Start in the Maine Coast Book Shop and Cafe, where you can peruse a large collection of books, and take your book of choice to their cafe. This is a great spot to read and experience the local culture of this coastal town.

If you couldn’t find the book you were interested in at this location, you can head over to the Skidompha Secondhand Book Shop. This book shop looks over the Damariscotta River and has a collection of thousands of second-hand books. And if books aren’t your thing, you can look through their supply of puzzles, movies, and music. Best of all, all proceeds go to the local library!

Another gem of a store in the heart of this small town is Aboca Beads. This large shop is designed to explore artistry in jewelry. You will find handmade beads from all over the world, as well as some made locally in Maine.  

If you aren’t in the mood to shop, you could check out the Salt Bay Farm and Nature Center

This center spans over 11 acres and is known for its beauty. It offers stunning views of the rolling hills located around the area and the saltwater habitats that have been looked after for hundreds of years. 

Finally, head over to the Damariscotta River Grill to end the day. This restaurant is loved by locals and tourists alike. Here, you will find classic seafood meals and bar-and-grill plates. 

Rockland

About 30-40 minutes away from Damariscotta is Rockland. This mid-coast Maine destination is the next stop on your road trip. 

Take a lovely stroll around Rockland Harbor. At the end of the harbor sits the Rockland Breakwater Lighthouse. This lighthouse is well over 100 years old and is charming and unique. The trip down to the lighthouse and back is roughly two miles, so it’s a great chance to take a walk, soak up some sun, and appreciate the vintage Windjammers. 

If you can time it correctly, try to be in Rockland during the Maine Lobster Festival. This festival takes place over five days during the first weekend of August. Just like the name suggests, there are over 20,000 pounds of lobster there for people to eat. In addition, while you are at the festival, you can watch a cooking contest, buy products from local vendors, watch a parade, and do so much more.

If you can’t make it to the Lobster Festival, you can check out the Farnsworth Art Museum, Project Puffin Visitor Center, or the Center for Maine Contemporary Art. 

During the evening, be sure to sign up for the Main Foodie Tour located in Rockland. This tour will take you to all the best spots in Rockland. You will try the best restaurants, charming pubs, and culinary shops.

You also don’t have to worry about making it through the night with only a few tastings of food; this tour will ensure you have at least one full-sized meal (if not more). 

Camden

Just 15 minutes up the coast from Rockland is Camden. 

Start your day by grabbing a blanket and takeout from a local restaurant and head to the Camden Harbor Park and Amphitheater. Start by walking along the harbor and taking in the views of the water, and then make your way up to the Amphitheater.

From the amphitheater, you can take in the views of the park, harbor, and bay. Once you are in the park, sit down on the blanket and have a nice picnic. Grab an ice cream cone stroll along Main Street (well regarded for its shops).

Next, make a stop at Uncle Willy's Candy Shoppe. This retro candy shop will transport you back into simpler times. Here, you can find both modern and classic candies, so if you have been looking for your favorite candy that is rarely sold anymore, you might be able to find it here. It’s eccentrically decorated and is a fun space for children and adults. 

At the end of the day, try to see a show at the Camden Opera House. This is a large auditorium that is filled with intricate moldings, chandeliers, and other impressive architectural features. At the Opera House, you can see a musical, ballet, comedy show, film, or concert. 

If you don’t want to see a show, you could book a sunset trip with The Schooner Surprise. The Schooner is available for two-hour trips in the water. You will be able to see marine life, lighthouses, and gorgeous views of coastal Maine. Getting the opportunity to sail on a historic schooner is rare, so take the opportunity while you can.

Camden Hills State Park is a must for those looking to visit Maine, especially for a taste of fall foliage

Bar Harbor

Bar Harbor is located two hours from Camden, making it the farthest stretch of driving yet. However, it is a beautiful town with plenty of attractions, so the drive is definitely worth it. 

The best way to start your day in Bar Harbor is to walk along the Shore Path. Shore Path is a coastal trail that wraps around the southern and eastern shores of the island. This viewpoint has inspired countless artists who paint the scenes of Maine. You can also look out over the water and see the other islands, making the view even more impressive. 

Next, if you are up for more walking, head over to Acadia National Park, located on Mount Desert Island. Here you can find rocky beaches, granite peaks, and woodlands. It also contains the tallest mountain on the East Coast: Cadillac Mountain. Don’t forget to stop by Jordan Pond House, the only full-service restaurant in this park.

There are plenty of trails for hiking, mountain biking, or horseback riding. However, if your feet are hurting at this point, you can take a tour of the park with Oli’s Trolley. Explore the gorgeous scenery in a charming, old-fashioned trolley.

Last but certainly not least, now is your time to schedule a whale watching tour with Bar Harbor Whale Watch Company. Experts on the boat will guide passengers into the center of whales’ habitats to see various types of whales, such as humpback, finback, and Minke. Even if you don’t spot a whale, you are guaranteed to see a dolphin, seal, offshore bird, or puffin. 

Conclusion 

By this point, you should be convinced that Maine has everything to offer for a road trip. If you want to sit leisurely on a beach with a book, you can check out York, Kennebunkport, or Bailey Island.

If exploring local shops sounds most exciting, you will love downtown Portland and Damariscotta. Or, if you are itching to take some hikes and explore nature on foot, then Bar Harbor is right up your alley. 

This trip through Maine will also allow you to experience unique things to the area, such as whale tours, locally sourced lobster, and views of historic New England architecture. 

No matter what you are interested in during your trip through Maine, be sure to have HearHere queued up to make driving through the state entertaining and exciting. This way, you can experience the culture and history of Maine as you drive through it. You’ll learn the answers to questions you never considered and get inspired to ask even more.

Sources:

Beaches | Town of York Parks and Recreation

Home | Portland Head Light 

Salt Bay Farm & Nature Center | Coastal Rivers Conservation Trust

Home | Maine Lobster Festival

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