Downtown Boothbay Harbor, Maine, via j76n /

10 Most Picturesque Small Towns in Maine

Maine, the United States’ 12th-smallest and 9th-least populous state, is also the most expansive and northeasternmost state in the American Northeast’s New England region. Boasting jagged Atlantic & Bayshore coastlines, rugged Appalachian Mountains, rolling hills, fertile river valleys, thick coniferous forests, and numerous crystal-clear waterbodies, the dazzlingly beautiful state of Maine aptly justifies its nickname, “The Pine Tree State.” Coastal Maine's amazing shorelines, speckled with ancient lighthouses and miles of pristine sandy beaches, in addition to being the location of urban metropolises such as Portland, have always been the top choice of vacationers visiting Maine. So, if you wish to explore Maine more closely, do embark on a journey to spend your vacation in any of the innumerable picturesque small towns that dot this spectacular state.

Boothbay Harbor

View of Boothbay Harbor, a tourist fishing town in Lincoln County, Maine, United States
View of Boothbay Harbor, a tourist fishing town in Lincoln County, Maine, United States, via EQRoy /

Lovingly referred to as the “Boating Capital of New England,” this picture-perfect Lincoln County town occupies the southern tip of a peninsula in the Gulf of Maine, bounded by the Linekin Bay to the east and the Sheepscot River to the west. During summers, holidayers head to Boothbay Harbor in large numbers to catch a glimpse of the region’s plentiful marine life, unwind by the waters, and taste some delectable seafood. Walk down the waterfront area and browse the multiple shops like Sherman’s Maine Coast Book Shop, and Gimbel & Sons Country Store, apart from the myriad eating joints like Boothbay Lobster Wharf, Downeast Ice Cream Factory, and Boathouse Bistro Tapas Lounge & Restaurant. Stroll across Boothbay Harbor’s famous footbridge and tour noteworthy sites like the Boothbay Harbor Railway Village & Museum, Opera House at Boothbay Harbor, Carousel Music Theater, and Abacus Gallery. 


The marina in Castine, Maine.
The marina in Castine, Maine.

Formerly named ‘Majabigwaduce’ by the native Tarrantine Abenaki Indians, Castine in Hancock County is one of the oldest towns in New England, occupying a peninsula in Penobscot Bay approximately 130 miles north of Portland. With over 100 historic markers peppered all over, this National Register-listed town exudes an exclusive old-world appeal via its conscientiously maintained historic sites, churches, parks, vintage-style houses, deep water harbor, Castine Post Office, and the Wilson Museum. The town also houses the 185-acre Witherle Woods Preserve with more than 4.3 miles of hiking and cross-country skiing trails, the principal campus of the Maine Maritime Academy, the 1828 Dyce Head Lighthouse, Wadsworth Cove Beach, Backshore Beach, the Maritime Academy’s 500-foot naval research ship (TS State of Maine), and Castine Golf Club.


Buildings on Main Street in downtown Damariscotta, Maine.
Buildings on Main Street in downtown Damariscotta, Maine.

Damariscotta, “The Oyster Capital of New England,” is situated near the mouth of Damariscotta River in Lincoln County, roughly 12 miles from the Atlantic coast. For several decades, Damariscotta has been a favored tourist spot among holidayers and Mid-Coast Maine inhabitants, owing to its abundant supply of fresh Pemaquid oysters and a unique small-town allure. Originally a distinguished shipbuilding hub, the town has a large number of buildings in varied architectural styles including Chapman-Hall House, the town’s oldest building constructed in 1754. The Whaleback Shell Minden State Historic Site, Skidompha Secondhand Book Shop, Damariscotta Farmers’ Market, Frances Perkins Center, Lincoln Theater, and Kefauver Studio & Gallery are some of Damariscotta’s must-visit places of interest. A variety of festivals like the Damariscotta Mills Fish Ladder “Alewives” Festival, Pemaquid Oyster Festival, and Damariscotta Pumpkinfest & Regatta are hosted by the town every year.


Fisherman in Stonington, Maine.
Fisherman in Stonington, Maine.

A scenic coastal Maine fishing town in Hancock County, Stonington, formerly known as “Green’s Landing” is located on Deer Isle Island’s southern edge in eastern Penobscot Bay. Regarded as one of the premier lobster ports in the nation and the biggest lobster port in the state, the town is well-known for its quaint working waterfront and well-preserved landmark properties lining the narrow, meandering streets of the downtown. When in town, browse the noted art galleries like Geoffrey Warner Studio (OWL Furniture), watch concerts at the Stonington Opera House, hike the forest-covered trails of the neighboring Barred Island Preserve, and indulge in lip-smacking dishes at the town’s award-winning restaurants such as Fin & Fern, Harbor Café, 44 North Coffee – Stonington Café, Stonington Ice Cream Company, etc.


Downtown Camden, Maine.
Downtown Camden, Maine.

Dubbed the “Jewel of the Maine Coast,” Camden is a tranquil holiday destination in Knox County and a renowned summer colony in Maine’s Mid-Coast region for opulent Northeastern US residents who come to spend quality time at the elegant mansions. Located beside Penobscot Bay at the base of Camden Hills, this pretty town of 5,232 inhabitants as per the latest US Census, has been named in honor of the First Earl of Camden – Charles Pratt, for his crucial support during the American Revolutionary War. The town’s harbor business district and strollable downtown are jam-packed with uncountable 19th-century architecture, specialty shops, locally-owned boutiques, galleries, and eateries serving standard New England dishes. Camden Harbor Park & Amphitheatre, Camden Opera House, Camden Public Library, and the adjacent Camden Hills State Park are some remarkable attractions. The town hosts yearly events such as the Camden Windjammer Festival, Camden Harbor Arts & Crafts Show, Christmas by the Sea, US National Toboggan Championships, and Camden Winterfest. 


Kennebunkport: Shopping plaza on sidewalk street in downtown village during summer day
Kennebunkport: Shopping plaza on sidewalk street in downtown village during summer day, via Kristi Blokhin /

In southwestern Maine’s York County, Kennebunkport is an enchanting seaside resort town approx. 1 mile from the Kennebunk River’s mouth on the Atlantic Ocean and 29 miles southwest of Portland. Originally a fishing and shipbuilding village, the settlement gradually became a famed summer colony for the affluent class and one of the wealthiest communities in the state. When visiting the town, travelers can spend time perusing the various souvenir shops, small boutiques, art galleries, seafood restaurants, cozy bed & breakfasts, and schooner attractions in the Dock Square area. Kennebunkport’s interesting points include St. Ann’s by-the-Sea Episcopal Church, Cape Porpoise – to the southwest of the immaculate Goose Rocks Beach and northeast of Dock Square, and the Walker’s Point Estate – considered to be the summer retreat of the Bush Family. Outdoor lovers can head straight to the adjoining Rachel Carson National Wildlife Refuge for wildlife and migratory bird-watching, while merrymakers can attend the many annual festivals like the Kennebunkport Festival, Memorial Day parade, and Kennebunkport’s Christmas Prelude.


Wiscasset skyline in fall
Wiscasset skyline in fall

Often called “Maine’s Prettiest Village,” the administrative center of Lincoln County is situated along the western shores of the tidal Sheepscot River in Maine’s Mid-Coast region. Located only an hour away from the state’s most populous city, this initial shipbuilding, fishing, and lumber trading hub was the busiest seaport to the north of Boston until 1807. Currently, a substantial portion of Wiscasset forms a part of the 101-acre Wiscasset Historic District, which features numerous noteworthy landmark properties like the Nickels-Sortwell House, Wiscasset Public Library, Castle Tucker, Capt. George Scott House (Octagon House), Lincoln County Courthouse, Wiscasset Jail & Museum, etc. The town’s other notable sites of interest include the Wiscasset Antiques Mall, Rendall Fine Art Gallery, Maine Heritage Village, Marston House Wiscasset, 1790 Tiny House, and the state’s only zipline & adventure park – Monkey C Monkey Do. In addition, grab some mouthwatering meals at classic restaurants like Marketplace Café, Sprague’s Lobster, Sea Basket, and Water Street Kitchen & Bar – Wiscasset.

Bar Harbor

Main street of Bar Harbor, Maine.
Main street of Bar Harbor, Maine.

This pleasant coastal retreat in southern Maine’s Hancock County is situated on the northeastern shores of Mount Desert Island, at the foothills of the 1,530-foot-tall Cadillac Mountain along Frenchman Bay. Officially incorporated on February 23, 1796, as the ‘Town of Eden,’ the settlement was rechristened in 1918 as ‘Bar Harbor’ after the sand and gravel bar visible during low tide. A popular vacation destination, thousands of holidayers flock to Bar Harbor from May to October, especially due to the town’s proximity to the magnificent Acadia National Park. With more than 50 miles of car-free carriage roads and 120 miles of hiking trails, the Acadia National Park offers visitors a wealth of outdoor recreation like biking, bird watching, hiking, mountain climbing, horse riding, and kayaking. Tourists who wish to witness the region’s rich marine life and the incredible scenery of coastal Maine must take part in nature cruises and maritime tours at a local marina. Furthermore, being the eastern terminus of the Northern Tier Bicycle Route of the Adventure Cycling Association and the Atlantic Coast Bicycle Route’s northern terminus, Bar Harbor draws countless long-distance cyclists from worldwide throughout the year. 


Exterior of Steam Mill Antiques historic farmhouse in Bethel, Maine, nestled in the White Mountains
Exterior of Steam Mill Antiques historic farmhouse in Bethel, Maine, nestled in the White Mountains. Editorial credit: jenlo8 /

Bethel, an idyllic alpine town is located on the western extremity of the Oxford Hills and the southern margin of the White Mountains’ Mahoosuc Range. Aside from these craggy mountains, the town’s closeness to the White Mountain National Forest has made it a top-tier year-round outdoor mecca and the perfect starting point for varied recreations. In the neighboring wilderness areas, tourists can partake in hiking, canoeing, mountain biking, fishing, and kayaking activities during the warmer months, while excellent alpine skiing can be experienced during winter at the Sunday River Ski Resort, Carter’s XC (Cross-Country) Ski, and Mt. Abram Maine resort. Additionally, do visit the town’s other interesting attractions like the Museums of the Bethel Historical Society, Table Rocks Arts Center, Hastings Homestead Museum, Gibson’s Apple Orchard, Maine Mineral & Gem Museum, the Gem Theater, Grafton Notch State Park, and Middle Intervale Meeting House & Common. All four seasons, Bethel’s alluring walkable downtown offers some outstanding lodging and dining options with the Bethel Inn Resort, Sud’s Pub at The Sudbury Inn, Crossroads Diner – Bethel, Good Food Store, and Butcher Burger.


Aerial view of Greenville, Maine.
Aerial view of Greenville, Maine.

Set on the southern tip of Moosehead Lake – the state’s biggest freshwater body- this pretty Piscataquis County town at the core of Maine Highlands- is a gateway to the North Maine Woods and a haven for outdoor recreation enthusiasts. Home to 1,437 inhabitants, Greenville is a popular resort destination that features a series of colonial architectures abutted by dense forests and glistening water bodies. When in town, the first stop must always be the Moosehead Lake Indian Store at Kamp Kamp – a one-stop shop supplying everything from souvenirs, antiques, jewelry, and furniture to outdoor gear needed to explore the Moosehead Lake area. Adventurists can enjoy a hike up the Big Moose Mountain, visit the Katahdin Cruises & Moosehead Marine Museum, Lily Bay State Park, Moosehead Historical Society & Museums, Spotted Cat Winery, and the nearby Mt. Kineo State Park, take seaplane tours offered by Jack’s Air Service, etc. The Young’s Guide Service offers nature lovers opportunities to observe and photograph the region’s rich faunal wealth, especially moose. 

From Boothbay Harbor – “The Boating Capital of New England” to Wiscasset – “Maine’s Prettiest Village,” Maine has ample picturesque small towns that are waiting to be discovered by sightseers. Whether you are on a visit to Maine for a weekend trip or a long vacation, check out these gorgeous towns that will surely captivate you with their impressive natural beauty, fascinating histories, colorful celebrations, and appetizing seafood cuisines.

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