5 Must See Coastal Towns to Experience Classic New England

5 Must See Coastal Towns to Experience Classic New England

Maine Towns That Embody New England coastal charm

Greater Portland Island, Beach, and City Escapes

Lobster shacks. Sandy Beaches. Sea breezes. Tall ships. Squawk of a seagull overhead. That’s classic New England. That quaint coastal vibe you can find in made-for-tv movies or—along the shores of Casco Bay in Greater Portland, Maine. 

Bite into Maine Lobster rolls, Photo Credits: Serena Folding

Photo Credit (Clockwise from top): Serena Folding (1), Lauren Peters (2-3)

When it comes to trendy beach towns and classic New England vibes, Greater Portland, Maine, is where it’s at. Nestled between rugged coastlines and sandy shores, it is a place that beckons you to kick back, slow down, and soak in the ocean air. 

Portland, Maine is a small city hub. The peninsula is a little over 3 miles, so everything from the working waterfront to the historic cobblestone streets are easily accessible. Nearby towns, just a short drive away, have their own slice of coastal magic waiting to be explored.


1. Freeport

New England Shopping + Seaside Excursions 

Freeport is renowned as a shopper’s paradise, but it’s also a coastal haven. Freeport has the best of the best in brands and boutique shops. At the heart of the town stands the legendary L.L.Bean flagship store, a 24/7 gem for outdoor enthusiasts. But, beyond retail therapy, Freeport offers a delightful round-up of waterfront restaurants, outdoor adventure, and charming annual New England fairs + festivals. 

Fresh seafood at local landmarks like Linda Bean’s Made in Maine and the Harraseeket Inn as well as scenic oyster farm tours and waterfront cruises provide a unique glimpse into Maine’s local fare and maritime heritage. It also makes the picture-perfect backdrop for the group pic.

Linda Bean's Perfect Maine

Visit our amazing restaurants in Portland, Freeport, and Port Clyde for Maine lobster. Try our famous lobster roll.

Harraseeket Inn

Luxury country Inn with two award-winning restaurants, located two blocks north of L.L. Bean in the village of Freeport.
Gritty's Lobster Bake. Photo Courtesy of Visit Freeport
Gritty’s Lobster Bake. Photo Courtesy of Visit Freeport

Nestled amidst its charming streets of their classic Main Street you’ll find year-round events like the The Maine Oyster Festival, Freeport Fall Festival, and the Sparkle Celebration, held during the holiday season. Whether you’re browsing the shops, enjoying a leisurely cruise along the coast, or savoring a meal with a view, Freeport captures the essence of coastal New England and Maine with its vibrant atmosphere and rich cultural offerings.

2 | Diamond’s Cove

New England Island Retreat

Knack Factory Shoot, Photo Credit: Lauren Peters at Visit Portland
Portland Cityscape, Photo Credit: Lauren Peters at Visit Portland

Just a short ferry ride from downtown Portland, Diamond’s Cove offers a tranquil island escape. This island destination is accessible via Casco Bay Lines, year-round commuter ferry providing service to the islands of Casco Bay. The journey becomes part of the experience when you hop on the Mailboat tour during . During the Summer and Fall it’s a narrated sightseeing cruise. Once ashore, visitors are greeted by pristine beaches, quaint cottages, and breathtaking ocean views that embody the quintessential Maine island experience.

Casco Bay Lines

Portland’s iconic ferry system with year-round ferry services, specialty cruises and private charters to the islands of Casco Bay.

Away from the crowds, Diamond’s Cove encourages a slower pace of life, perfect for relaxation and rejuvenation. Explore hidden coves, take a leisurely stroll along the shoreline, or simply unwind with a picnic overlooking the Atlantic. Stay at the Inn on Diamond Cove to extend the island time. A tranquil private island hotel, walking distance from the ferry, built in the former soldiers’ barracks in Fort McKinley, Great Diamond Island. Whether you spend a day or a weekend, Diamond’s Cove promises an unforgettable retreat where time seems to stand still, and every moment is filled with coastal serenity.

Inn at Diamond Cove

Split level suites, balconies, fireplaces and kitchenettes, a spacious lobby and a private in ground pool & cabana.

Diamond's Edge Restaurant

Combination of extraordinary service, fine food, and breathtaking views overlooking Diamond Cove.

3. Cape Elizabeth

New England Beach Destination

Cape Elizabeth is all about sandy toes and salty air. Picture-perfect beaches like the ones at Portland Head Light and Fort Williams Park offer more than just stunning views—they’re a piece of New England history. Whether you’re exploring the lighthouses or just chilling by the waves, Cape Elizabeth delivers that quintessential coastal experience you’ve been dreaming of.

Portland Head Light and Fort Williams Park epitomize the coastal charm and New England vibes that define Cape Elizabeth. The iconic Portland Head Light, the oldest lighthouse in Maine, stands majestically against a backdrop of cliffs and the expansive Atlantic Ocean. The historic significance and picturesque beauty of the lighthouse and Fort Williams Park draw visitors year-round, offering breathtaking views and countless photo opportunities. You can even grab a lobster roll oceanside at the Bite Into Maine food stall on-site.

Bite Into Maine

Nationally recognized and specializing in traditional and unique lobster rolls that will tempt your taste buds.

Inn by the Sea in Cape Elizabeth is a beachfront oasis that perfectly blends luxury and coastal charm. Nestled along the pristine shores, this eco-friendly resort offers breathtaking ocean views, elegantly appointed accommodations, and exceptional amenities. Guests can relax on the sandy Crescent Beach, stroll through beautifully landscaped gardens, and indulge in locally sourced cuisine at the on-site restaurant.

Inn by the Sea

Luxury resort on Southern Maine Coast with spectacular ocean views. Full-service Spa & Sea Glass Restaurant.

Sea Glass at Inn by the Sea

Sea Glass Restaurant at Inn by the Sea offers an unsurpassed Maine dining experience with spectacular ocean views.

4. Falmouth

New England Outdoors + Water Adventures

With its mix of outdoor adventures, scenic beauty, and a welcoming community, Falmouth Foreside truly captures the essence of a classic New England destination. Whether you’re exploring the coastline, engaging in seasonal activities, or simply enjoying the stunning views, Falmouth promises an unforgettable experience that highlights the best of coastal Maine.

Falmouth Foreside is set against the breathtaking backdrop, providing glimpses of Portland’s Calendar Islands, including Long Island, Clapboard Island, and Sturdivant Island. The area is renowned for its elegant homes and expansive coastline – along with the invigorating scent of sea air.

During the summer, Falmouth buzzes with events and activities like golf, sailing, kayaking, and paddleboarding. The pristine beaches and well-maintained parks are perfect for jogging, picnicking, or simply relaxing with your furry friend. In winter, the town transforms into a snowy wonderland, offering ice skating, tubing, and scenic winter walks along the coast.

5. Scarborough

Marine Wildlife + Authentic Maine

If outdoor adventures are your jam, Scarborough is your playground. Ferry Beach is your go-to spot for sandy shores and serene sunsets. And don’t miss checking-out the Scarborough Marsh—a massive estuary bustling with wildlife. Perfect for kayaking, canoeing, or just taking a leisurely stroll. It’s nature at its finest, just waiting for you to explore.

Scarborough, a quintessential New England town, offers a delightful mix of iconic attractions and charming experiences. Home to the famous Len Libby Chocolatier, visitors can indulge in delectable homemade chocolates and marvel at Lenny, the life-sized chocolate moose. Holy Donut is a local donut shop, specializing in Maine potato donuts.

They are both a local favorite and a viral sensation – you have to taste-test the seasonal flavors when you’re in town. There’s multiple locations, including their spot right on Commercial Street downtown, one of them being just down the road from the iconic Len Libby in Scarborough, so you can get the best of both worlds in terms of sweet treats.

Len Libby Candies

You’re guaranteed a moose-sighting at Len Libby Candies, home of Lenny, the world’s only life-sized chocolate moose! We have a huge selection of chocolates and more.

Holy Donut @ Exchange St

Our delicious donut flavors rotate, with 20 options available to choose from at the start of each day.

Maine is Classic New England at its Finest

Greater Portland, Maine’s area towns are a love letter to authentic New England. Capturing the nostalgic cobblestones and historic buildings that make this East Coast gem and can’t-miss destination. From the hustle of Portland to the hidden treasures of area towns—each offering its own blend of history, culture, and natural beauty that’s impossible to resist—Greater Portland is the ultimate escape for anyone craving a slice of New England by the sea.

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