Summary
- Fall in Maine is the perfect time to explore the state's charming towns and cities, with their scenic, historic streets and vibrant main streets. Wander downtown areas packed with shops, galleries, and restaurants.
- Coastal villages and mountain hamlets showcase a range of architectural styles, from ornate brick buildings to colorful clapboard storefronts. These areas also host farmer's markets, art walks, concerts, and cultural festivals.
- Visiting Maine's picturesque downtowns is a must for travelers looking to experience the state's many treasures. Browse locally owned boutiques, cafes, and breweries, and admire the historic architecture that gives each town its unique charm.
One of the best free things to do in Maine during the fall is to stroll down its towns' and cities' scenic and historic streets. From Maine's oldest-founded towns to its bustling modern cities, the state has many charming areas with beautiful downtowns and vibrant main streets. These beautiful historic business districts invite visitors to park their cars and stroll from shop to shop, gallery to gallery, and restaurant to restaurant.
From coastal villages to mountain hamlets, the architecture ranges from brick buildings with ornate detailing to colorful rows of clapboard storefronts. Beyond shopping and dining, many beautiful downtown areas in Maine host farmer's markets, art walks, concerts, and festivals celebrating community and culture.
For travelers looking for some of the best trips in Maine to take in the fall, visiting these pictorial downtowns is a must. Wander the quaint sidewalks and discover locally owned boutiques, cafes, breweries, historic architecture, and more that provide a taste of Maine's many treasures.
10 Boothbay Harbor
This bustling seaside downtown overlooks the picturesque harbor and has gardens and grand old houses. The narrow main street beckons visitors to pop into boutiques, fudge shops, and restaurants housed in historic buildings.
Don't miss the Coastal Maine Botanical Gardens on the outskirts, which displays ornamental gardens, native woodlands, and waterfront trails. The popular Boothbay Railway Village also offers short train excursions from the town's old restored depot.
- Location: On the coast in Midcoast Maine
- Top Attractions: Coastal Maine Botanical Gardens, Boothbay Railway Village
- Things to Do: Ride the railway, explore the gardens, browse shops and galleries
9 Wiscasset
Situated on the banks of the Sheepscot River, Wiscasset boasts one of the most beautiful downtowns in Maine; it is a nationally recognized main street lined with colonial architecture and antique shops.
Sample the famous Red's Eats lobster roll stand, which has been in business since the 1920s. Art lovers will appreciate the plethora of downtown galleries, including the Center for Maine Contemporary Art. Home to the musical Hideaway Concert Series, Wiscasset also provides great opportunities to listen to top regional bands in an intimate venue.
- Location: On the Sheepscot River in Midcoast, Maine
- Top Attraction: Musical Hideaway Concert Series
- Things to Do: Listen to live music, browse antique shops
8 Naples
On the shores of Long Lake, Naples' small but lively downtown stretches along Route 302. Visitors can browse the boutiques, admire the lake views, or enjoy a cone from one of Maine's most popular ice cream stands, The Naples Scoop. July 4th brings big crowds for the famous Naples Fourth of July Parade, featuring lively floats.
Nearby, walk the historic causeway over Brandy Pond or explore the Songbird Nature Center trails, surrounded by stunning fall foliage.
- Location: Near Long Lake in western Maine
- Top Attraction: Naples Fourth of July Parade
- Things to Do: Browse shops, walk the lake causeway
7 Bucksport
This town on the Penobscot River contains a charming downtown full of 18th and 19th-century buildings. Stroll the brick sidewalks and visit shops stocked with work from local artisans.
Save time for the unique Bucksport Waterfront Walkway following the river, where there's a giant replica of a sea monster. Don't miss Fort Knox, an impressive 19th-century fort upriver providing scenic hiking trails with panoramic views.
- Location: On the Penobscot River in coastal Maine
- Top Attraction: Bucksport Waterfront Walkway
- Things to Do: See the sea monster sculpture, explore Fort Knox
6 Kingfield
Surrounded by mountains on the Carrabassett River, Kingfield's small downtown consists of several blocks of historic one and two-story buildings. Pop into the galleries, boutiques, and cafés along Main Street, which serves some of the best lobster rolls in Maine, or listen to live Music at the restored 1914 Stanley Museum.
Nearby, hike Mount Abram trails winding past Kingfield Pond and waterfalls or bike the scenic Fifteen-Mile Stream trail system. In winter, Kingfield serves as the gateway to the Sugarloaf ski resort.
- Location: In the mountains of western Maine
- Top Attractions: Mount Abram, Fifteen Mile Stream trails
- Things to Do: Hike, bike, ski at Sugarloaf
5 Belfast
This lively seaside town overlooking Penobscot Bay contains an architecturally diverse downtown lined with independent shops, galleries, restaurants, and more. As one of the most beautiful downtown areas in Maine, visitors can enjoy harbor views along the waterfront path or find creative gifts at downtown boutiques like The Green Store or Mocean.
On summer Friday evenings, residents and visitors gather for free Music by the Bay concerts at Heritage Park on the bay's shores.
- Location: On the coast in Midcoast Maine
- Top Attraction: Belfast Harbor waterfront
- Things to Do: Stroll the harbor path, enjoy free summer concerts
4 Rockland
At the heart of the midcoast, Rockland's tree-lined streets filled with striking Greek Revival homes lead down to the always-bustling harbor. Stroll the acclaimed Farnsworth Art Museum and stop into the many galleries dotted throughout downtown.
Enjoy a lobster stew lunch on a seaside deck before browsing the boutiques and cafes in historic brick buildings along Main Street. Don't miss the beloved Maine Lighthouse Museum downtown, showcasing the state's iconic beacons.
- Top Attractions: Farnsworth Art Museum, Maine Lighthouse Museum
- Things to Do: Visit museums, art galleries, boutiques
3 Camden
With its picture-perfect harbor and pristine historic buildings, Camden is often considered one of New England's oldest towns to serve as a vacation destination. Visitors can indulge in the lively downtown's many local shops, renowned restaurants, and waterfront inns. Be sure to hike up Mt. Battie for stunning high views over the harbor and surrounding mountains dotted with the fiery colors of autumn.
Fall also brings foodies to the popular Camden International Film Festival downtown.
- Top Attractions: Picturesque downtown, Mt. Battie
- Things to Do: Hike Mt. Battie, shop downtown, attend the Camden International Film Festival
2 Stonington
On a granite peninsula jutting into the Atlantic, this seaside village contains a quaint downtown stretching down Main Street.
Browse the historic buildings' galleries, shops, and wooden boat showrooms before enjoying fresh seafood with harbor views. Visitors can also take a narrated boat tour into nearby islands like Isle au Haut or hop the mailboat ferry to Swan's Island for a scenic ride and day trip.
- Location: Coastal village on a granite peninsula
- Things to Do: Take boat tours, ride the mailboat ferry
1 Castine
With roots as a Revolutionary War site, Castine offers a glimpse into 18th-century history through its well-preserved downtown. Follow the walking tour to see standout examples of Colonial and Federal architecture. Enjoy the small-town pace browsing the shops and galleries, or take a break for a craft beer and lobster roll on a hillside deck overlooking the harbor.
Don't miss stopping by Dyces Head Lighthouse, a stocky conical tower and one of the few lighthouses open to the public in Maine.
- Top Attraction: Well-preserved historic downtown
- Things to Do: Take the walking tour, browse shops and galleries