Ultimate Bucket List Road Trip: 15 Must See Coastal Detours in Maine
Ultimate Bucket List Road Trip: 15 Must See Coastal Detours in Maine
Discover Coastal Beauty, Island Escapes, and Local Charm Across Greater Portland and Casco Bay
Planning to hop in the car and drive up the coast this Summer? Well, get your playlist and road snacks ready—when it comes to scenic trips, few regions in New England offer as much variety when it comes to local charm and coastal magic as Greater Portland and the Casco Bay region. Outdoor adventure and metropolitan flair easily accessible and never more than minutes away.
Whether you’re planning a summer escape, a weekend getaway in Maine, or a full family vacation itinerary—these 15 stops are the perfect places to pause, explore, and connect with what makes Maine unforgettable.
Photo Credits (Clockwise from top): Kirsten Alana Photography (1-3), GLP Films (4)
From iconic lighthouses and sandy beaches to quiet hiking trails, green spaces, and indie sports there’s something for everyone. Experience the best of our area towns and ferry-accessible islands (yes, you can bring your car). This is your go-to guide for turning your Maine road trip into an experience you’ll take with you forever.
1. Fort Williams Park in Cape Elizabeth, Maine
Cape Elizabeth is a road tripper’s dream and a standout highlight of any New England itinerary. Just minutes from downtown Portland, this iconic coastal town is the perfect place to stretch your legs, breathe in the salty breeze, and feel like you’ve truly arrived in Maine. Known for its windswept beauty and cinematic coastline, Cape Elizabeth is home to Portland Head Light—the most photographed lighthouse in the country and an essential stop on the East Coast Lighthouse Trail.
Set within Fort Williams Park, the area offers miles of scenic paths, historic ruins, picnic-perfect lawns, and cliffside overlooks that deliver panoramic views of the Atlantic. Whether you’re here for a quick stop or a full afternoon, it’s the kind of place that recharges your spirit and captures the essence of Maine’s rugged charm. Start here.
2. Spring Point Ledge Light in South Portland, Maine
South Portland blends seaside serenity with small-town energy, making it an ideal stop for road trippers craving both relaxation and discovery. Just over the bridge from downtown Portland, this coastal gem offers sweeping views of Casco Bay’s outer islands, pedestrian-friendly shorelines, and a quieter pace that invites you to stay a little longer.
Stop at Saltwater Grille in South Portland for their seafood classics and panoramic views of Portland harbor from across the way. One of the area’s most rewarding experiences is the walk to Spring Point Ledge Light—a scenic breakwater lighthouse that gives visitors a chance to venture out into the bay and see Portland’s working harbor from a truly unique angle. Whether you’re catching the golden hour glow on the water or taking in the sound of gulls over the shipyards, South Portland captures the spirit of Maine’s maritime legacy in a deeply personal way. Start here.
3. Scarborough Marsh in Scarborough, Maine
Scarborough is where Maine’s wild coastline stretches wide, offering road trippers a deep breath of fresh air just south of Portland. The town is home to the expansive Scarborough Marsh, the largest salt marsh in the state and a haven for kayaking, birdwatching, and peaceful boardwalk walks surrounded by sweeping grasses and quiet wildlife.
Beyond the marsh, beaches like Ferry Beach and Pine Point Beach offer soft sand, low surf, and plenty of room to stretch out between road trip destinations. And if you’re craving a sweet roadside detour, Len Libby is the place to pull over for a photo with Maine’s most famous life-sized chocolate moose. Scarborough pairs nature and nostalgia with effortless ease—making it a worthy stop on any coastal drive. Start here.
4. Presumpscot River in Westbrook, Maine
Westbrook is a must-stop for road trippers craving something unexpected just outside Portland. Tucked beside the Presumpscot River. This revitalized town is gaining momentum with walkable downtown streets, creative energy, and riverfront views that feel both calming and alive. Public art installations, local trails, and open-air events make it a great place to stretch your legs and change up the pace of your coastal adventure.
At the heart of Westbrook’s transformation is Rock Row—a bold new development built around a massive natural quarry. With its mix of retail, eats, green space, and future-forward design, Rock Row is quickly becoming one of Maine’s most exciting destinations for events and entertainment. Start here.
5. Gambo Preserve Trail in Gorham, Maine
Gorham invites road trippers to slow down and experience southern Maine’s peaceful inland side. Just west of Portland, this scenic town is known for winding country roads, rolling farmland, and forested outlooks perfect for spontaneous stops. It’s a refreshing detour for travelers looking to stretch their legs and immerse themselves in the quieter rhythms of New England.
Gorham trails offer a variety of options right off your drive. Hit the Gambo Preserve Trail for riverside views and a dose of history, or explore the Presumpscot River Trail, which links to nearby towns and offers access to waterfalls and woodlands. The Shaw Cherry Hill Farm Trail is another quick-hit hike for families or solo travelers wanting big views in a short loop. For road trippers craving fresh air and authentic rural beauty just beyond the coastline, Gorham delivers a rewarding change of pace. Start here.
6. Eastern Promenade in Portland, Maine
You can’t drive through Maine, without hitting its largest city. Portland is where your road trip energy meets the city’s creative pulse. From the East End’s sweeping views of Casco Bay to the sandy curve of Portland’s only beach, East End Beach. The Eastern Promenade is ideal for relaxing, walking, and watching windjammers, lobster boats, and kayaks drift in and out. For a higher perspective, visit the historic Portland Observatory to take in views of the rooftops, harbor, and nearby islands.
Down on the working waterfront, you’ll find lobster boats, fish markets, and the daily rhythm of the port that keeps the city connected to its roots. Portland is one of the most vibrant small cities in the country—and a can’t-miss stop for any traveler heading up the coast. Start here.
7. Macworth Island in Falmouth, Maine
Just north of Portland, Falmouth offers a calming shift from city energy to coastal quiet—making it a perfect roadside pause for travelers heading up or down the Maine coast. One of the area’s true hidden gems is Mackworth Island, a beloved short loop trail that wraps through shaded forests, along rocky shores, and past hand-built fairy houses tucked among the trees. With sweeping views of Casco Bay and tidal inlets, this trail feels like walking through a storybook.
Falmouth is ideal for road trippers who want to reconnect with the natural landscape without veering too far off route. Whether you’re traveling solo, adventuring with kids, or simply need a moment of stillness between destinations, Falmouth provides scenic serenity just minutes from downtown. Start here.
8. Broad Cove Reserve (or Fall Fair) in Cumberland, Maine
Cumberland is full of timeless Maine beauty, offering a peaceful pause on your road trip just north of Portland. Known for its rolling farmlands, winding roads, and classic red barns, the town feels like a living postcard—especially in late summer and early fall, when roadside farm stands spill over with harvest produce and the air turns crisp and golden. The Cumberland Fair comes alive with one of Maine’s most beloved agricultural fairs, making it a seasonal draw for families and travelers alike.
Beyond the fair, Cumberland is a scenic outdoor hub. Hike or bike through local nature preserves like Rines Forest or Broad Cove Reserve for a deeper connection to the land. The town’s understated charm and natural rhythm offer road trippers a thoughtful moment to reset—and a reminder that some of Maine’s best views aren’t always on the coast. Start here.
9. Royal River Park (or Clam Festival) in Yarmouth, Maine
Yarmouth blends riverside calm with small-town personality, offering road trippers a refreshing mix of coastal nature and community charm just 20 minutes north of Portland. Tucked along the Royal River, this historic town invites you to slow down and soak in its creative, walkable energy. Start with a scenic stroll through Royal River Park, where shaded trails, waterfalls, and picnic nooks offer the perfect chance to stretch your legs mid-drive. Then wander Main Street, lined with historic buildings, local boutiques, and glimpses of daily life in one of Maine’s most welcoming communities.
If your road trip lines up with July, Yarmouth transforms into a festival hotspot during the annual Clam Festival, a beloved Maine tradition featuring parades, music, and—you guessed it—plenty of seafood. But even outside of festival season, the town’s blend of history, nature, and neighborhood energy makes it worth the detour. Whether you’re looking for peaceful river views or a low-key afternoon off the highway, Yarmouth delivers a sense of place that’s as warm as it is memorable. Start here.
10. Outdoors + Waterfront in Freeport, Maine
Freeport may be famous for its outlet shopping, but it’s also one of the most exciting outdoor gateways on the Maine coast. Just 30 minutes north of Portland, this town makes a perfect road trip stop for travelers who want to balance big-name retail with open-air adventure. Main Street is anchored by the legendary L.L.Bean Flagship Store—open 24 hours a day—so whether you’re arriving early or rolling through late, you’ll always find the lights on and the boots waiting.
To really get your blood pumping, sign up for a session at the L.L.Bean Outdoor Discovery Programs, where you can try your hand at archery, fly casting, kayaking, or snowshoeing depending on the season.
For a deep connection with the landscape, just a few minutes down the road you’ll find Wolfe’s Neck Center—a coastal escape where trails meander through white pine forests, salt marshes, and tidal inlets. It’s the perfect contrast to the buzz of downtown and a reminder that Freeport’s best features might just lie beyond the storefronts. Start here.
11. Bradbury Mountain in Pownal, Maine
For road trippers chasing scenic hikes near Portland, Maine, Pownal is the kind of inland detour that pays off in peaceful trails and panoramic views. Just a half-hour drive from the city, Bradbury Mountain State Park is one of the most popular day hikes in southern Maine—perfect for a leg-stretch and a look across the treetops. Whether you’re starting your journey or breaking up a coastal itinerary, this stop adds movement, elevation, and fresh mountain air to your road trip mix.
With trails like the short-and-scenic Summit Trail or the longer, wooded Northern Loop, there’s something here for every kind of hiker. The summit offers sweeping views over forest and farmland, and on a clear day, you’ll catch glimpses of Casco Bay in the distance. If you’re looking to pair coastal beauty with inland adventure, Pownal connects it all in one simple, satisfying stop. Start here.
12. Land’s End on Bailey Island, Maine
Bailey Island is classic Maine at its most elemental—salty, scenic, and worth every curve in the road to get there. The drive alone is one of the most memorable along the southern coast. You’ll follow a winding shoreline through Harpswell (just an hour north of Portland), passing coves, causeways, and inlets, until you reach the island via the historic Cribstone Bridge—a granite engineering marvel built to let tides pass through. As you cross, lobster traps line the roadside and the wide Atlantic opens up beside you, signaling you’ve arrived somewhere special.
Once you’re on the island, life slows down. Park the car and take a seaside walk along Land’s End, explore coves framed by glacial rock, or simply watch the rhythm of fishing boats leaving and returning to harbor. It’s not just a place to visit—it’s a mood, a moment, and a memory in the making. Whether you’re road-tripping from Portland for the day or weaving Bailey Island into a longer coastal journey, this is one detour that delivers the soul of the sea. Start here.
13. Deer Point on Chebeague Island, Maine
Just a short ferry ride from Portland (or Cousin’s Island in Yarmouth), this serene Casco Bay island invites travelers to step off the grid and into a slower rhythm. With rocky beaches, quiet woodlands, and gently winding roads, Chebeague is tailor-made for long walks, shoreline wandering, and quiet moments where time feels suspended.
The island’s unplugged charm is its biggest luxury. For a quiet adventure, head to Deer Point—a protected 13-acre property on the island’s southwest tip. Park near Bennett’s Cove and follow the wide dirt path through wind-shaped trees until you reach the ocean ledge. It’s long been a local favorite for picnics, salt air, and uninterrupted horizon views. For a classic Maine coast pause, drive the 3 miles up to the Chebeague Island Inn Restaurant and Bar for a drink on the porch—complete with panoramic water views and the sound of seabirds overhead. It’s a place to reflect, recharge, and reconnect with the kind of calm that only an island can offer. Start here.
14. South Beach on Long Island, Maine
Long Island feels like a best-kept secret just waiting to be part of your road trip detour. Accessible by ferry from Portland, this Casco Bay island offers a laid-back vibe and quiet natural beauty—ideal for travelers wanting a low-key escape just off the beaten path.
Spend time at South Beach, the island’s most popular stretch of sand, where you can swim, sunbathe, or beachcomb in peaceful surroundings. Don’t miss a stop at Byers & Sons Long Island Bakehouse, where locals and visitors alike refuel with lobster rolls, chowder, or a fresh breakfast sandwich before catching the ferry back. Whether you’re staying the day or just the afternoon, Long Island offers that elusive “disconnected” feeling—without ever being too far from the mainland. Start here.
15. Mailboat Run in Portland, Maine
Every great coastal road trip deserves a moment at sea. If you’re not sure which island to explore first—or you just want a breezy, beautiful way to take it all in—catch an afternoon ride on the Casco Bay Lines Mailboat Run. Departing right from the Portland Working Waterfront, this scenic cruise delivers mail, cargo, and passengers to the year-round residents of Casco Bay’s working islands, giving you a firsthand look at local life on the water.
It’s the perfect way to preview stopovers like Peaks, Cliff, or the Diamond Islands—all in one loop—and soak in stories of the so-called Calendar Islands, a myth that claims there are 365 islands in the bay: one for every day of the year. While the true number is closer to 200, the spirit of that legend rings true. Out here, every island feels like its own little world—and your next great detour could be just one ferry ride away.
Final Word: The Drive Is the Destination
Greater Portland and Casco Bay offer the kind of road trip where every turn holds something beautiful. From inland farms to lighthouse cliffs, ferry rides to island trails, this region rewards curiosity and invites you to slow down and explore. Whether you’re visiting for a weekend or just passing through, these 15 stops will help you connect to Maine’s coast in a way that feels personal, memorable, and beautifully local. Start planning today.
