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If you want a relaxing weekend with some amazingly beautiful ocean scenery, a road trip up coastal Maine is absolutely perfect. Not only will it be quieter and more peaceful than many of our other suggested cities. It’s largely rural and not touristy, the cost of food, lodging, and activities is much lower than in most cities. Be sure to stock up on Healthy Road Trip Snacks.
Starting in Stop 1: Portland, Maine
We’ll start our Road Trip in Portland, Maine. Mainly because there are only two large airports in Maine; Portland [PWM] & Bangor [BGR]. One is located near the bottom of the state and one near the middle. Bangor is not near the top, despite what some people will tell you. I used to live in the top of Maine, it’s several hours north of Bangor.
There are of course some smaller airports throughout; Presque Isle (now that’s the top), Ellsworth, Owls Head, etc. But they have limited flights, and most fly outside of the state.
If you head towards Boston, here is a list of destinations worth visiting in our post about Boston Road Trips.
Obtain a car (likely rent one), but you will need a car. You won’t see a subway/metro at any point. Once you leave downtown Portland, you likely won’t see any local public transportation. You really cannot get around Maine without a car. There are also so many great day trips from Portland that are only possible by car. If you choose to stay in Portland to explore check out our 48-Hour Guide to Portland.
Want to try a unique tour of Portland? Try this tour on the back of a vintage fire truck.
Fill up with gas, maybe grab some snacks and let’s go! Jump on I-295 North and we’ll be on our way. Note that Portland sits between I-95 and I-295, so make sure you’re getting on the right one. There are actually places where they connect and you’ll see signs for both in Portland, including near the airport. But for our trip, we’ll need to be on I-295, so make sure you get on the right one.
If you’re interested in some of the towns near Portland heading south, check out York, Maine.
#2 Freeport, Maine
We’ll head north for 18 miles and take Exit 22 in Freeport. Freeport is the home to the L.L. Bean World Headquarters as well as all of its flagship stores. All of the L.L. Bean stores are open 24/7/365. In June 2020, due to the pandemic, for the first time ever, L.L. Bean installed locks on the doors of their flagship store. Prior to that, the last time they officially closed was back in 2015 so employees could attend the funeral of the company founder.
L.L. Bean has a campus of five stores in Freeport. You can buy everything from bed sheets to tents to a canoe or mountain bike. Of course, no trip to the L.L. Bean store is complete without a picture next to the huge bean boot outside of their flagship store.
While in Freeport, there are lots of amazing stores to see. A McDonalds was built inside a Victorian house. There is also a WhoopiePie Store, Mangy Moose Gifts, and lots of Outlet Stores. All are within walking distance, so plan on spending some time there. You can easily spend a day without seeing everything you wanted to see. But, we’ve got to get going. Back onto I-295.
#3 Yarmouth, Maine
Barely a couple of miles up from Freeport, keep an eye out on your right-hand side for “Eartha.” Eartha is the world’s largest rotating globe at the Garmin Headquarters (Previously DeLorme). You’ll see it just past Exit 17. (If you want a close-up view, feel free to take Exit 17, it’s just barely off the exit.) Otherwise, continue north on I-295, and take Exit 28. Wave goodbye to the Interstate because that’s the last you’ll see of it during this road trip. It’s all scenic back roads from here on out.
#4 Brunswick, Maine
Just a little way up Route 1 is historic Bowdoin College, which was chartered in 1794. At the time, Maine was still a part of Massachusetts. On campus is the Bowdoin College Museum of Art (which has free admission for all). They have a pretty impressive collection of art.
#5 Topsham & Bath, Maine
From here on out, we’ll be sticking to Route 1, which goes from the top of Maine to the bottom of Florida. In Maine, it snakes along the coastline. We’ll be sticking close to it for the rest of the trip for lots of great ocean views. It’s not an efficient way to get from the bottom of Maine to the top, but it’s definitely the most beautiful.
So, hopping on Route 1 North in Brunswick, we’ll head up through Topsham, and Bath (The City of Ships). On your right, as you approach the bridge from the elevated highway, you’ll see Bath Iron Works. Bath Iron Works (BIW) is the fifth-largest defense contractor in the world and the builder of the Zumwalt Series of Navy Vessels. Most of the time, you’ll see their current project docked out in the river.
Next up is Wiscasset, where you should prepare for a traffic jam. Downtown Wiscasset historically backs up traffic in both directions for miles. Sadly there is no real way around it as there is only one bridge across the water in the area.
PRO-TIP: Do not go to the roadside stand that is Red’s Eats. It’s absolutely a tourist trap. The lines are always very long, the food is overly expensive, and the product isn’t worth the price. It’s also a big contributor to the massive traffic backup.
#6 Waldoboro, Maine
Continue up Route 1, enjoying the small coastal towns along the way. A stop at Moody’s Diner just north of downtown Waldoboro for a late breakfast or lunch is highly recommended. Great food and even better prices. They are famous for their pies, so make sure you save some room for that. They also serve Ice Cream and for some reason, they also have a motel, cabins, and a gift shop. After getting some food, jump back on Route 1 North and we’re going to head up to Thomaston.
#7 Thomaston & Rockland, Maine
Once you hit Thomaston, I suggest checking out the Maine State Prison Showroom. It’s all products made by prisoners who are working on rebuilding their lives by learning a skill. There are some pretty incredible things in that store that shows off their skills. Next, we’ll come to Rockland, and let’s get a good look at that ocean view. Stop by the Harbor Park (Address: 1 Pleasant St, Rockland, ME 04841) and take in the view.
Depending on when you stop by, there are commonly fairs and festivals going on at the park. Most notably the Maine Lobster Festival. If you really want to get up close to the water, take a walk down the Rockland Breakwater. The breakwater is a 4,364-foot rock bridge directly into the ocean with a lighthouse at the end. But, before that, take some time to really peruse downtown Rockland. Beautiful coastal town, and very walkable, so park the car and go look around.
PRO-TIP: The Rockland Breakwater is an incredible experience to really feel like you’re in the ocean and the views are amazing. But, plan your trip carefully. It is a reasonably narrow (about 43 feet wide) uneven rock ledge and at high tide, water does splash onto the rocks making them slippery. You’ll want to be careful heading out there.
#8 Camden, Maine
Continuing up Route 1, we’ll stop in Camden, another cute little walkable town along the water. Another place that you’ll want to stop and check out is the little shops and galleries. Continuing up the road, we’ll pass through a few more little towns and villages along the coast. Keep an eye out of your right-side windows for beautiful views of the ocean. Pass through the city of Belfast and across the bridge with views of the marina, and through Searsport. Bear right towards Ellsworth instead of turning onto Route 1A towards Bangor.
Happen to visit in the Winter? Camden Snow Bowl is on our list of the best Ski Resorts in New England
Keep an eye out for the scenic lookout that looks out over the Penobscot Narrows Bridge & Observatory. This bridge is the tallest public bridge observatory in the world. At night it’s lit up in multi-colored floodlights. If you’ve got the time, going up to the top of the observatory will give you 360-degree views of the river and the bay, and central Maine. You can also tour historic Fort Knox which serves as the parking and entry for the observatory. It’s covered in the cost of the observatory ticket. After crossing over the bridge, drive just one mile on Verona Island before crossing back over another bridge into Ellsworth.
If you miss the turn towards Ellsworth, you’ll end up in Bangor, Maine. But, that’s not so bad a destination either.
#9 Ellsworth, Maine
Ellsworth is home to the Great Maine Lumberjack Show with regular shows that include “12 exciting events packed into an hour and 15-minute show.” It includes Axe throwing, Log Rolling, Underhand Chopping, Power Hot Sawing, Obstacle Pole Relay, Crosscut Sawing, Pole Climbing… And More!”
This is also a good city to stop in if you need any supplies as it’s one of the bigger cities along this trip. It includes some of the more common large department stores. If you’re looking for a classic Maine Restaurant, I would suggest Govenor’s Restaurant. Make sure you take a look at their always-changing dessert case. If you’re feeling very adventurous (or with a big group), take a look at the Federal Deficient.
#10 Mount Desert Island, Maine
If you happen to have lots of free time left on your road trip, just south of Ellsworth is Mount Desert Island. Otherwise, known as MDI, it’s home to Acadia National Park. Acadia includes lots of beaches and lighthouses. Definitely a beautiful area to check out if you have the time. Try this self-guided driving audio tour, or a narrated bus tour if you want to take a break from driving for a few hours.
Otherwise, let’s continue following Route 1 North up through the little towns of Gouldsboro, Milbridge, Cherryfield, and into Columbia. Columbia is home to the Wreaths Across America Program, and the hundreds of thousands of wreaths shipped to Washington DC are produced here in Washington County and start their journey from this location.
Where to stay near Acadia National Park
➡️ The Inn on Mount Desert
➡️ Atlantic Eyrie Lodge
#11 Machias, Maine
You have to stop at Wild Blueberry Land, if nothing else for some pictures. You won’t be able to miss it. If they are open, they also have a blueberry store and museum inside. As you can likely tell now, you can get a sense of what rural Maine really looks like out here. Continue up to Machias and be sure to stop at Helen’s Restaurant. Established in 1950, this place has flooded once, burned down once, and moved locations once, and still is one of the mainstays of Machias. They have award-winning pies, so at least stop for one of those if not dinner.
#12 Final Stop: Calais, Maine
Continue up Route 1 towards Calais, the last stop on our Coastal Maine Road Trip. While driving, keep an eye out for the beautiful ocean and island views on your right side. This is what rural Maine is all about. If you want proof of just how far north you are, stop by the 45th Parallel Marker, indicating halfway between the equator and the north pole. Once you pass that point, everything you see across the water from you on the right side is actually Canada. The last stop is Calais. The reason that this is the last stop on a Coastal Road Trip is that beyond this point, you’re either in Canada or heading back inland. Calais is the biggest city in Washington County with just over 3,000 people in total.
Coastal Maine Road Trip: In Conclusion
So, there we end. You started in the largest city in Maine (Portland, ME) and passed through some of the smallest villages in Maine with a total population of fewer than 500 people each. You saw a lot of our beautiful coastal towns, each with its own unique personality. Because of a previous job covering coastal Maine, I’ve made this drive dozens of times. I’ve never stopped being amazed by the beauty and the amazing people and places that I’ve seen on my journeys.
I would highly recommend blocking out at least a full weekend or more to make this drive. If you really want to experience Coastal Maine, you could spend weeks here.
