10 Best Day Trips under 30 Minutes from Portland, Maine

10 Best Day Trips under 30 Minutes from Portland, Maine

10 Best Day Trips Thirty Minutes (or less) from Portland, Maine

As a major historic, cultural, and culinary destination – Portland, Maine serves as the perfect homebase to view charming New England area towns across the region. Embark on a journey through the vibrant coastal communities and scenic landscapes surrounding Portland, Maine, where each destination offers its own unique charm and New England allure. 

Gritty's Lobster Bake. Photo Courtesy of Visit Freeport

Photo Credit (clockwise): Visit freeport, Serena Folding, PGM Photography, Serena Folding

From bustling shopping meccas to tranquil hiking trails and historic landmarks, these day trips under 30 minutes promise unforgettable memories and endless opportunities for exploration. Join us as we delve into the hidden gems that await in Greater Portland’s charming neighboring towns.

Seaside Adventure at Wolfe's Neck Woods State Park. Photo Provided by Visit Freeport

1 | Freeport

Shopping + Waterfront Adventures


Known for its shopping, local seafood, and picturesque waterfront, Freeport is a haven for visitors looking to explore more of Greater Portland. Just a short drive from Portland, Freeport beckons with its water views along the rocky coast. Start at the iconic L.L.Bean flagship store, a mecca for outdoor enthusiasts offering everything from gear and apparel to outdoor experiences.

Photo Courtesy of Visit Freeport

Enjoy a leisurely lunch at one of the local restaurants, savoring fresh seafood and local flavors. Check out one of Visit Freeport’s events for art, shopping, music, and more. For outdoor enthusiasts, Freeport offers opportunities for kayaking, paddleboarding, and boating along the sparkling coastline. Whether you’re seeking retail therapy, waterfront adventures, or simply a scenic escape, Freeport has something for everyone just 30 minutes from Portland.


Summit views at Bradbury Mountain. Photo Courtesy of Visit Freeport

2 | pownal

Hiking and Outdoor Adventure


Venture into the wilderness of Pownal for exhilarating hiking trails and outdoor escapades. With an abundance of natural beauty, Pownal offers opportunities to get out in the great outdoors of Maine for a little wildlife spotting amidst serene landscapes. Lace up hiking boots and explore the scenic trails of Bradbury Mountain State Park, offering panoramic views of the countryside from the summit.

Photo courtesy of Visit Freeport

For a more leisurely adventure, pack a picnic and enjoy a scenic stroll along the park’s tranquil paths. Pownal also boasts opportunities for mountain biking, birdwatching, and wildlife spotting, making it an ideal destination for nature lovers and outdoor enthusiasts alike. If you’re seeking a challenging hike or a peaceful retreat in nature, Pownal offers a scenic escape just a short drive from Portland.


Pratt's brook Park Photo Credit Serena Folding

3 | North Yarmouth + Yarmouth

new england fall foliage


Experience breathtaking fall foliage in North Yarmouth and Yarmouth. Take a leisurely drive through winding roads adorned with vibrant hues of red, orange, and gold, or embark on a scenic hike to immerse yourself in nature’s autumnal splendor. Embrace the beauty of autumn with a day trip to North Yarmouth and Yarmouth, stop to enjoy the splendor of the season at local restaurants like Gather serving-up harvest-themed seasonal menus.

Photo Credit Serena Folding

Stop by local orchards + farms to pick apples, sip fresh-pressed cider, and sample homemade pies bursting with fall flavors. For outdoor enthusiasts, Pratt’s Brook Park is Yarmouth’s largest park offering 6 miles of hiking trails while meandering through forests vibrant with autumn hues. The town is dotted with historic buildings, quaint shops, and cozy cafes. Whether you’re snapping photos of picturesque panoramas or indulging in seasonal treats, Yarmouth offers a quintessential New England fall experience.


Cumberland Fair, Photo Credits: Serena Folding

4 | Cumberland

fall Fairs + harvests


Celebrate the spirit of fall at the Cumberland Fair, a beloved annual event in Cumberland. Indulge in classic fair delights, from carnival rides to agricultural exhibits, and savor the festive atmosphere of this quintessential New England fair. Held annually in the scenic town of Cumberland, check out our Fairs + Festivals page for more events held all over the Pine Tree state.

Photo Credits: Serena Folding

Stroll through rows of vendor booths offering handmade crafts, local goods, and savory treats, indulging in fair favorites like fried dough and caramel apples. Enjoy thrilling rides and games on the midway, with attractions for both children and adults alike. Immerse yourself in the sights, sounds, and flavors of the season as you create cherished memories with family and friends. 


Falmouth Town Landing, Photo Credit: Serena Folding Photography

5 | Falmouth

tranquility + island escapes


Discover hidden coves, panoramic vistas, and the enchanting village nestled amidst Macworth island’s natural beauty. Just a short drive from Portland, this idyllic coastal haven offers breathtaking views of of Maine’s rocky coast and a peaceful ambiance perfect for relaxation and rejuvenation. Take a leisurely stroll along the island’s trails, winding through lush forests and meadows adorned with wildflowers.

Photo Credit: Serena Folding Photography

Pause to admire panoramic vistas of the bay and take a slow approach to travel. Pack a picnic and enjoy a seaside feast at one of the island’s scenic areas, or simply find a quiet spot to bask in the beauty of nature. Whether you’re seeking solitude, inspiration, or simply a moment of tranquility, Macworth Island offers a peaceful escape just moments from the heart of Falmouth.


Downtown Westbrook. Photo Credit: CFW Photography

6 | westbrook

entertainment Hub


Treat yourself to a day of shopping and entertainment in Westbrook, a vibrant community brimming with retail destinations, tasty treats, and attractions. Explore the bustling streets of downtown Westbrook, where boutique shops and galleries beckon with unique treasures and locally crafted goods.

Photo Credit: CFW Photography

Have you visited Rock Row? Westbrook’s one-stop-shop for all things eat, drink, and shopping. This development is expanding and events like Quarryside at Rock Row – live music and beer garden – are being added to the lineup, so stay tuned. 


Sidecar Pub. Photo Credit: Knack Factory

7 | gorham

trails + indoor entertainment


Unleash your adventurous spirit in Gorham, where an extensive network of trails beckons outdoor enthusiasts. Nestled away just minutes from Portland, Gorham beckons outdoor enthusiasts and adventure seekers with its diverse array of attractions and activities. Lace-up your Bean boots and explore the town’s extensive hiking and walking trails, winding through green forests and rolling hills.

Photo Credit: Knack Factory

For thrill-seekers, Junction Bowl games offers adrenaline-pumping fun with its state-of-the-art VR gaming experiences, immersive arcade, and bowling. Afterward, unwind with a craft cocktail at Sidecar Pub, Gorham’s premier destination for artisanal spirits and live music. With its perfect blend of natural beauty and urban amenities, Gorham offers the ideal day trip destination for those looking to escape the city and immerse themselves in the great outdoors.


Marshland, Photo Credits: Serena Folding

8 | scarborough

Marshlands + Wildlife


Experience the natural beauty and abundant wildlife in Scarborough, a coastal gem located just a 15-20 minute drive from Portland, Maine. Discover the pristine marshlands and serene trails of Scarborough Marsh, New England’s largest saltwater marsh, where you can observe a diverse array of bird species, including egrets, herons, and ospreys.

Photo Credits: Colleen Mars

Embark on a guided kayak tour of the marsh, paddling through winding waterways and hidden channels as you learn about the area’s rich ecological significance. After a day of exploration, unwind with a leisurely stroll along Scarborough’s sandy beaches or just soak in the sparkling waters of the Atlantic Ocean. Whether you’re a nature lover, birdwatcher, or outdoor enthusiast, Scarborough offers endless opportunities for outdoor adventure and wildlife encounters just minutes from Portland.


Portland Head Light Snowy Photo Credits: Serena Folding

9 | cape elizabeth + south portland

historic landmarks


Immerse yourself in the rich maritime heritage and breathtaking coastal scenery of Cape Elizabeth and South Portland, two charming towns located within a stone’s throw of Portland. Begin your day with a visit to Cape Elizabeth’s iconic Portland Head Light, Maine’s oldest lighthouse, perched atop majestic cliffs overlooking the Atlantic Ocean. Stroll along the scenic trails of Fort Williams Park, where you can admire sweeping ocean views and explore historic military ruins.

Photo Credits: Serena Folding

Then, indulge in a classic Maine culinary experience with a lobster roll from Bite Into Maine, a local food truck situated within the park. In South Portland, discover more iconic lighthouses – Spring Point and Bug Light, where you can wander along scenic pathways and enjoy panoramic views of Casco Bay. Don’t miss the opportunity to explore Bug Light Park or walk the rocky path leading to Spring Point Ledge Light. Cape Elizabeth and South Portland offer a wealth of unforgettable experiences just minutes from downtown Portland.


Fore River Sports Fishing cruising on water, Photo Credit: PGM Photography

10 | Casco Bay Islands

island adventures


Discover hidden coves, historic forts, and stunning coastal vistas as you cruise along Casco Bay to one of Portland’s local islands. An island escape is always only a short ferry ride away. Indulge in beachfront lobster bakes, kayak along tranquil shorelines, or simply relax and soak up some island time with a craft cocktail or mocktail.

Photo Credit: PGM Photography

Whether you’re seeking outdoor adventure, cultural exploration, or simple relaxation, the Casco Bay Islands offer the perfect escape from the hustle and bustle of mainland life, just a short Casco Bay Lines ride from Portland.



As you explore the wonders of Greater Portland’s surrounding communities, you’ll find yourself immersed in the rich tapestry of Maine’s coastal beauty and vibrant culture. Extend your trip and explore even more of Maine in other regions. Plan your trip today.