Located in the Northeastern US, Maine is often called Vacationland—and with good reason. The Pine Tree State's diverse natural landscapes, epic outdoor adventures, and cozy, welcoming towns make it the perfect place to spend any vacation. From famed destinations like Acadia National Park to the crystal clear waterways of Moosehead Lake, bustling beach towns like Bar Harbor to coastal seaside communities like Kennebunkport, Maine's cozy small towns have something for everyone looking for a breathtakingly beautiful escape from the ordinary.
Greenville
Greenville, nestled within the ruggedly beautiful Maine Highlands, also has the distinction of being located on the state’s largest lake. Moosehead Lake—measuring approximately 40 miles long and 20 miles wide—is the centerpiece of the picturesque community and is also a hub for the area’s best outdoor recreation. While boating and fishing are popular activities, several hiking trails allow visitors to explore the lake’s scenic beauty. Popular trails include the Little Moose Mountain Loop, the Moxie Falls Trail (complete with a 90-foot waterfall), and the Mount Kineo Trail (around an hour away from town), complete with a fire tower offering panoramic views of the Moosehead Lake region. Lily Bay State Park also offers year-round activities, from swimming and boating in summer to cross-country skiing and snowmobiling in winter.
Greenville and Moosehead Lake are also some of the best places to spot moose in the area, and there are many spots where visitors can catch a glimpse of the Pine Tree State’s official mammal. Additionally, one of the best ways to explore is via a guided tour. Visit the Moosehead Marine Museum, home to the National Historic Landmark steamboat The Katahdin in addition to a variety of historic scenic tours. Those who wish to learn more about local history can also visit The Moosehead Historical Society & Museums and their lineup of historical properties highlighting the Moosehead Lake area’s rich culture and heritage.
Castine
Located in Maine’s Downeast Acadia region, Castine’s breathtaking seaside views perfectly complement its quaint, elm tree-lined streets—creating a quintessential Maine village worthy of a postcard. And with just over 1,000 residents, Castine is the definition of cozy. But don’t let that fool you: plenty of activities and attractions are scattered throughout this quaint Penobscot Bay community.
One of the oldest towns in New England, Castine has plenty of history. Learn more about local lore at the Wilson Museum and the Castine Historical Society; pay a visit to the Castine Post Office, the oldest continuously operating post office in the US; or head to picturesque Fort Madison, whose history is only exceeded by its coastal views. Castine is also home to the Maine Maritime Academy, where visitors can take a tour or simply catch a glimpse of its training ship, the impressive State of Maine.
Visit Castine's lighthouse, Dyce Head Light, for even more seaside views (and history). Though located on a private residence, the historic lighthouse is open to the public and even has a scenic footpath. After exploring Castine’s lovely harbor, head to Wadsworth Cove Beach, a pretty, secluded spot perfect for swimming, sunbathing, and even more stunning views. In the summer, outdoor enthusiasts can also enjoy kayaking, sailing, and maritime tours.
Boothbay Harbor
Defined by its proud maritime heritage, colorful harbors, and beautiful coastal views, Boothbay Harbor is one of Maine’s coziest towns. The Boothbay Peninsula is home to a treasure trove of activities, whether a stroll through the Coastal Maine Botanical Gardens, with its vibrant displays and scenic walking trails, or the Boothbay Harbor Region Sculpture Trail, a year-round public art exhibit. The Opera House at Boothbay Harbor and the Boothbay Region Historical Society Museum also offer a glimpse of the area’s unique history and culture.
Boothbay Harbor is also a great place to explore other area attractions. Connected to the peninsula via a historic swing bridge, Southport is a nearby island with a personality all its own. Visit the Hendrick’s Hill Museum for some local history, explore the Linekin and Burley Preserves’ scenic trails, or check out some of the region’s prettiest lighthouses, Cuckold’s Lighthouse and Burnt Island Light. Those looking for a day at the beach will also enjoy a day trip to nearby Pemaquid Beach and its neighbor, Pemaquid Point Lighthouse Park. For more fun on the water, take a tour of Linekin Bay, an area famed for its spectacular whale, puffin, and seal-watching opportunities. There are also plenty of local tours to explore more islands in and around Boothbay Harbor.
Rockport
Located less than 40 miles south of Augusta, Rockport is a bustling coastal town often referred to as “The River.” And while Rockport does have plenty of history—it was settled in 1769— it is the Knox County town’s reputation as an artist’s colony that sets it apart, with institutions like Bay Chamber Concerts and the Rockport Opera House serving as cornerstones of the community. Rockport also celebrates its heritage with annual musical celebrations and events, like Jazz in June and the North Atlantic Blues Festival.
With its Penobscot Bay setting and breathtaking coastal views, Rockport’s harbor serves as a scenic backdrop to the town’s parks and beaches, each with its own diverse landscapes and recreational opportunities. Stroll the trails at Beech Hill Preserve, enjoy the beach at Walker Park, or take a swim at Glen Cove Beach & Park. Visitors can also visit the statue of Andre the Seal, who spent his summers in Rockport serving as its honorary Harbor Master.
Rockport is also close to other beautiful communities situated along Maine’s Route 1. Nearby Camden has plenty of unique experiences, including Camden Hills State Park, the Camden Windjammer Festival, and the US National Toboggan Championships. Merryspring Nature Center is also a must-see natural retreat, with its arboretum, themed gardens, and four miles of scenic trails.
Stonington
Located on the southern tip of Deer Isle, Stonington is a cozy fishing community of just over 1,000 residents. But there’s more to this small waterfront village than its famed lobster fleet. Known as the “gateway” to the Merchant’s Row archipelago, Stonington has a distinctive beauty all its own that includes everything from vast, forested landscapes to breathtaking coastal stretches—all with recreational activities fit for any outdoor enthusiast. Crockett Cove Woods, Barred Island Preserve, and Crystal Cove Preserve all offer exceptional hiking and scenery, while Stonington’s Merchant Row is home to more than 50 beautiful islands with picture-perfect landscapes and diverse recreational activities that include swimming, camping, sunbathing, sightseeing, and more.
While it may be known primarily as a fishing community, Stonington also has deep artistic roots. Colorful galleries, studios, and shops can be found throughout both Stonington and Deer Isle, while famed institutions like the Haystack Mountain School of Crafts offer tours of its picturesque facilities. The Stonington Opera House is another great place to bask in the small town’s eclectic atmosphere, while the Deer Isle-Stonington Historical Society offers a glimpse into its rich history.
Damariscotta
Damariscotta is a small community located in Maine’s mid-coast region. However, there is more to Damariscotta than its breathtakingly beautiful scenery. Known as the “Oyster Capital of New England,” the Lincoln County town is famed for its Damariscotta River oyster middens (or heaps of shells), dating back over 2,000 years—a historic marker of its past, but also its present status as an oyster fishing hub. Subsequently, the town honors its cultural heritage in a variety of ways, including the Whaleback Shell Midden State Historic Site (home of the famous middens), the annual Pemaquid Oyster Festival, and various tours on the Damariscotta River, where visitors can learn about everything oyster.
Though Damariscotta is all about the oyster, the picturesque region also has its share of activities on dry land. Some popular town trails include the Doyle Preserve, Huston Landing, and Round Top Farm, among others. Separated only by a bridge, Damariscotta’s twin village of Newcastle also has a charming downtown area, as well as popular attractions like the historic Lincoln Theater and St. Patrick’s Church, the oldest Roman Catholic Church in New England. While visiting, soak up even more coastal scenery with a visit to the River-Link Trail, which connects multiple scenic spots—you may even spot a moose (or two) along the way.
Bar Harbor
Located on Mount Desert Island, Bar Harbor is often referred to as the gateway to Acadia National Park. One of the most popular national parks in the US, Acadia National Park is also one of the most beautiful places in the Pine Tree State—and its dramatic mountains and cliff formations serve as a picture-perfect backdrop to Bar Harbor and its many attractions.
In addition to providing Bar Harbor with its signature scenic vistas, Acadia National Park also offers more than 49,000 acres of rugged landscapes and popular natural attractions. Whether it’s a scenic drive along Park Loop Road, an Ocean Drive sunset, hiking up Cadillac Mountain for views of Bar Harbor and the park, or visiting all seven of Desert Island’s lighthouses, there’s something for everyone in Bar Harbor and the neighboring Acadia National Park.
However, there’s more to Bar Harbor than its proximity to Acadia. Explore the community’s rich heritage with a visit to its many historical attractions such as the Abbe Museum, the Bar Harbor Historical Society, and the 1932 Criterion Theatre, listed on the National Register of Historic Places. Additionally, events like the Bar Harbor Music Festival, nearby attractions like the Cranberry Cove Ferry and the Woodlawn Museum, and diverse landscapes—from the picturesque Porcupine Islands to the famed Shore Path—all give Bar Harbor a signature Down East flair loved by locals and tourists alike.
Kennebunkport
Kennebunkport is a cozy coastal town in Southern Maine. A top tourist destination for over 100 years, the shipping community’s river and seaside location is the perfect backdrop for some of Maine’s most beautiful beaches. Located throughout Kennebunkport and its neighboring Kennebunk, some of the area’s most popular beaches include Kennebunk Beach (aka “Mother’s Beach”), Colony Beach, and Goose Rocks Beach, among others. Both the beaches and the Kennebunk River provide numerous recreation activities, including kayaking, stand-up paddleboarding, and spectacular views of the river and coastline. Visitors can also enjoy scenic water tours, along with whale watching and deep-sea fishing excursions.
Those who need a break from the beach and boardwalk will find plenty of diverse attractions throughout the area. Visit the Seashore Trolley Museum, complete with a vintage trolley tour, enjoy Museum in the Streets, a series of walking tours highlighting local history and heritage, dive into local cuisine with the Lobster Roll Trail, or discover Blowing Cave Park—in Kennebunkport, there’s something for every traveler looking for adventure.
Maine's Most Charming Beach TownsFrom petite fishing settlements to vivacious resort towns, Maine's coastal towns have something for every person.
Maine is known for its beautiful coastal communities and rugged, forested landscapes. However, there's more to the Northeastern state than its distinctive natural beauty: scattered throughout Maine are many cozy communities that offer visitors the chance to experience the state's best settings, outdoor recreation, and rich cultural heritage. Coastal towns like Rockport and Boothbay Harbor highlight the state's seaside scenery and maritime history, while small cozy villages like Damariscotta offer quintessential New England charm—each of Maine's most scenic small towns offers a unique way to experience the very best of the Pine Tree State.
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Lisa Wright June 16 2024 in Places
