7 Scenic Drives Around Boothbay Harbor (No Interstate Required)
You don’t have to go far to feel like you’ve really gone somewhere. Southport Island and its neighboring peninsulas are full of quiet, winding roads made for slow exploring — no interstates, no billboards, and no GPS confusion (well… not much, anyway).
Here are seven easygoing drives that show off the best of Midcoast Maine. Pack a snack, roll the windows down, and keep your camera handy.
1. The Southport Loop Road
This is your essential “get your bearings” drive. Start from the general store and loop the whole island—it only takes about 20 minutes without stops, but let’s be honest: you’ll stop. Hendricks Head Light, Cozy Harbor, and the swing bridge are all along the way.
2. Route 27 to Boothbay Harbor
This one’s your gateway to town. It’s less about the views (though you’ll still get some) and more about the anticipation of lunch, ice cream, or poking around the shops. Great for a morning outing or quick dinner run.
3. Barters Island Road + Back Narrows
Cross the little bridge onto Barters Island and enjoy one of the quieter drives in the area. You’ll pass peaceful coves, marshland, and houses that seem to lean into the trees. It’s a good one for a drive-then-walk kind of afternoon—consider stopping at the Trevett Country Store for a lobster roll or heading to the Porter Preserve trails.
4. Ocean Point Loop (East Boothbay)
A true gem. This coastal loop takes you right along the edge of the water, with rocky beaches, sailboats, and wraparound porches that make you consider abandoning modern life. It’s a local favorite for a reason—and ideal at golden hour.
5. River Road toward Edgecomb
This tree-lined stretch hugs the Sheepscot River and makes a quiet, relaxing route toward Wiscasset or beyond. You’ll pass farms, vintage homes, and a few blink-and-you’ll-miss-it roadside stands. Best enjoyed with a hot drink and zero agenda.
6. Lakeside Drive around Knickerbocker Lake
Tucked just inland from Boothbay, this is a mellow, forested loop that gives you a change of scenery from all the salt air. It’s especially peaceful early in the morning, when the lake is mirror-still and the light is soft.
7. Cross to Westport Island via the Back River Bridge
Not many visitors make it over here, which makes it even better. Follow Route 144 over the narrow causeway and you’ll find yourself on a quiet island with nature preserves, hidden beaches, and very little traffic. Bonus points if you bring a picnic.
Looking for more ways to explore the area? These drives are just the start. The real joy is in going slow, getting a little lost, and stopping whenever the view tells you to. Whether you’re catching golden hour at Ocean Point or watching the fog roll across the river, there’s something about seeing the region by car that makes it feel even more yours. Keep your windows down, your camera nearby, and your plans flexible — you never know what you’ll find around the next bend.
Let us know your favorite drive when you get back. We’re always collecting new detours.
Itching to hop in the car and be here already? Check our cottage’s availability or browse the blog for more ideas to build your perfect trip on the coast.