8 Beautiful Towns to Visit in Southern Maine in Fall

Southern Maine in fall brings an energy that not even the most idyllic summer can capture. As the chill of fall brushes the coast, it paints each town in a fresh palette of colors and vibrancy. Even beyond stunning fall foliage and churning seas crashing on rocky ridges, fall in Southern Maine is a harvest for the soul.

Each town celebrates the enrichment that autumn brings with festivals, fairs, and food feasts that grasp the last rays of sun before the days shorten in early November. As a bonus for fall visitors, Maine is now ranked as one of the top three safest states — even for solo travelers.

From festivals that are synonymous with the change of seasons to the subtle fall attractions you can explore in your own splendid solitude, here are the best towns to visit in Southern Maine in fall.

TIP: Southern Maine’s fall foliage is the last to peak in the state — the northern region starts in early September. The southern coastline shines in mid to late October.

Freeport

Freeport is home to the flagship store of L.L. Bean, which makes it a four-season destination. The town picks up steam as hunting season gets underway in Maine. However, it’s the Freeport Fall Festival surrounded by L.L. Bean Discovery Park that truly captures the essence of Maine during a three-day festival of arts, music, food, and fun with more than 200 vendors.

L.L. Bean’s Outdoor Discovery Programs host dozens of activities in the fall. Nearby, Wolfe’s Neck State Park bursts with fall colors on the water of Casco Bay. Ride a bike or paddle along the water at the Wolfe’s Neck Center, complete with a farm and barn open for tours.

The festival at Pettengrill farm opens up the saltbox farmhouse for one day only with a living museum of life in the 1800s.

Harpswell

When you truly want to immerse yourself in Casco Bay’s coastal fall vibes, Harpswell is heaven on earth with 216 miles of coastline — more than any other Maine town. The city spreads out like fork prongs, with three peninsulas and several islands to explore.

Between the town of Harpswell and the Harpswell Heritage Land Trust, there are 25 preserved lands — including nine islands — waiting with trails and jagged shorelines. You can walk or paddle your way around.

From Devil’s Bank trail to the wilderness-only isolation of Whaleback Island, the town also has scenic stops like Holbrook Street Landing, the Lands End Gift Shop, and Cook’s Lobster & Ale House with a view of the world’s only cribstone bridge.

When you want old-school Maine in the fall for scenic drives and dynamic trails peppered with working fishing towns along the way, Harpswell has it all.

The Yorks

Don’t let those Floridians tell you that there’s no good surfing in Maine. In fact, York Beach is one of the best places to hang ten in the fall. The popularity is anchored by the newly opened York Beach Surf Club along with great places to stay in The Yorks (the town of York and the villages of York Beach and York Harbor).

After Labor Day, all surfing restrictions are lifted since the beach crowds die down. Long Sands Beach is the most popular surf spot, and even if you just want to watch, paid parking restrictions end after mid-October.

Additionally, York Beach hosts a Harvestfest on Short Sands Beach. From the shore to the highest point in York, Mount Agamenticus offers 360° views of fall foliage. Be sure to listen for the call of the Great Horned Owl who starts nesting in September.

Other York highlights for fantastic fall sights include:

• A half-mile Cliff Walk from the beach to the rocky ledge
• Wiggle Bridge, the world’s smallest suspension bridge surrounded by water, rocks, and foliage
• Fisherman’s Walk scenic trail from the bridge to York Harbor Beach

Ogunquit

I once had someone from away tell me, “They say Ogunquit closes down after Labor Day.” I smirked, debating if I should point out that the town is so into fall that it holds THREE festivals to celebrate the season.

In Ogunquit Maine, the Capriccio Festival is a mix of performing arts and family-friendly activities, including the Festival of Kites on the beach each September.

Next, grab your Fall for Ogunquit Bingo Card. Fall for Ogunquit runs throughout October, with OgunquitFest kicking into high gear later in the month with an added Artisan Craft Fair.

The Marginal Way is open year-round, with pets allowed from October. Watching a fall sunrise from one of the benches is a great way to start the day.

TIP: Worried about the weather? Along the Southern Maine Coast, September temperatures are almost identical to June, with highs near 70 degrees and lows near 50. October is almost identical to May, with highs near 60 degrees and lows in the mid-40s.

Portland

Portland Maine in the fall is epic, and that’s not just the pumpkin beer or chocolate cinnamon sugar donuts talking.

This foodie destination brings its best game during Harvest on the Harbor, with newly shelled lobsters and the height of oyster season competing for awards. Portland’s best restaurants break out the best of fall menus, with Gilbert’s Chowder House offering six chowder choices.

Haunted tours are available in silly and spooky forms, along with historic tours through the unique districts. Paddle rentals, whale-watching tours, and schooner rides are offered through the end of October.

Many people don’t realize that Portland also has a series of islands, with Casco Bay Lines providing fall rides daily. Great views of Portland in fall are found on the nearly 4-mile-long Back Cove Trail that leads to the Eastern Promenade with beaches and lighthouse views.

For very early fall visitors, staying on the glamping island of Fortland is a unique experience.

Saco

Saco (“SOCK-oh”) was sad last fall when it looked like the second-oldest drive-in nationwide was closing after 80 years. The drive-in was saved just across the street from its original location. Shows run through September with the attached Aquaboggan Water Park picking up fall festivities during the annual Trail of Terror in October.

On Saco’s Main Street, the Pumpkin Harvest Festival takes over in late October. You can also sail away from Saco through early November on lighthouse, lobster, and scenic tours.

The system of Saco Bay Trails provides excellent explosions of fall color. After a rainy day, check out Cascade Falls.

Ferry Beach State Park brings a fall foliage twist, where you can walk through the Tupelo Swamp, a rarity this far north. Trails weave through forests and marshland before taking you to the beautiful beach.

DID YOU KNOW? While Maine’s state parks technically “close” around September 30, they are open year-round. You will just not have access to amenities or park rangers.

The Kennebunks

Fall is an excellent time to stay in Kennebunkport (“Ken-KNEE-bunk-port”). The summer crowds die down, and the foliage along Dock Square and the grand, historical homes give plenty of elbow room to chow down on massive lobster rolls.

Parents visiting for Halloween will love the more than 50 businesses between Kennebunk and Kennebunkport that offer trick-or-treating. Those beautiful sea captains’ homes on Summer Street in Kennebunk are open for all costumed kids and parents (and you KNOW you want to see those up close!).

NOTE: Kennebunkport charges for parking through the end of October.

Last but not least, a little-known fact is that Kennebunk is home to the Starfield Observatory, with star parties in the fall and a perfect spot to see the night skies with telescopes and a seating area provided.

The Berwicks

Berwick, South Berwick, and North Berwick have a hallowed fall feeling without really trying. The more unknown Vaughan Woods Memorial State Park provides some of the oldest and largest trees in Southern Maine, leading to fall foliage, but there’s more than that with each leaf-crunching step.

Along the Salmon Falls River, some of the first settlers arrived. Hamilton House majestically stands as an icon of the industry built from those steps. As if it’s not enough that the forest feels designed by the Brothers Grimm, you might even stumble upon some old family headstones.

In Berwick, you can take the lesser-traveled paddle path down the Salmon Falls River, soaking in the fall colors from New Hampshire and Maine as it straddles the state line.

Fall Fun Starts in Southern Maine

You can’t go wrong with any Maine town for a fall getaway. If you want the biggest festivals of the season, Portland’s Harvest on the Harbor ranks in the top three. The Fryeburg Fair in the Maine Lakes & Mountains region and the Damariscotta (“dam-risk-otta”) Pumpkinfest & Regatta on in the Mid Coast are the other two big events, and both are just a day trip from Portland.

But, festivals aren’t all that matter during fall in Southern Maine. Observe the vibrant leaves while enjoying recreational activities and get a taste of seasonal Maine foods during your visit.