Southern Maine

Destinations in Southern Maine

Things to Do in Southern Maine

Southern Maine is the most accessible region of the state — within easy reach of Boston and the broader New England population — and it delivers an exceptional range of experiences within a compact geography. The region runs from Kittery at the New Hampshire border north through York, Wells, Ogunquit, the Kennebunks, and Portland to Freeport and Brunswick, encompassing Maine’s finest beaches, its most celebrated food city, a world-class art museum, and some of the most charming historic towns in New England.

Portland

Portland is Maine’s largest city and one of the finest small cities in the United States — a compact, walkable urban center with a national food reputation, a world-class art museum, the Casco Bay ferry system, and the historic Old Port district. For visitors entering Maine from the south, Portland is the natural first stop and a destination in its own right. See our complete Things to Do in Portland Maine guide.

Ogunquit

Ogunquit is built around three exceptional assets: Ogunquit Beach (one of the finest in New England), the Marginal Way cliff walk, and a surprisingly strong arts and dining scene. The Ogunquit Playhouse has been producing Broadway-caliber summer theater since 1933. See our complete Things to Do in Ogunquit Maine guide.

Kennebunkport

Kennebunkport is the most refined town on the southern Maine coast — Dock Square, Ocean Avenue to Walker’s Point, Goose Rocks Beach, the White Barn Inn, Nunan’s Lobster Hut, and the authentic fishing village of Cape Porpoise. See our complete Things to Do in Kennebunkport Maine guide and our Kennebunkport vs Ogunquit comparison.

Freeport and L.L. Bean

Freeport is home to L.L. Bean’s legendary flagship store — open 24 hours a day, 365 days a year — and over 170 outlet stores in the surrounding blocks. The Desert of Maine, about 2 miles from downtown, is one of the most unexpected geological curiosities in New England. See our complete L.L. Bean Freeport Visitor Guide — open 24 hours a day, 365 days a year.

Beaches

Southern Maine has the finest beaches in the state. Ogunquit Beach is a 3.5-mile arc of fine white sand consistently ranked among the best in New England. Popham Beach State Park in Phippsburg is arguably the finest undeveloped beach in Maine — a sweeping arc of sand at the mouth of the Kennebec River with Fort Popham, Fox Island at low tide, and exceptional birding. See our complete Popham Beach State Park Visitor Guide — Maine’s finest undeveloped beach with Fort Popham and Fox Island at low tide.

Lobster

Southern Maine has some of the finest lobster roll destinations in the state. Red’s Eats in Wiscasset, The Lobster Shack at Two Lights in Cape Elizabeth, The Clam Shack in Kennebunk, and Barnacle Billy’s in Ogunquit are all within reach. See our complete Maine Lobster Roll Guide — Red’s Eats, The Lobster Shack at Two Lights, The Clam Shack, and the best in the state.

Portland Museum of Art

The Portland Museum of Art is one of the finest art museums in New England — a world-class collection with particular strength in Maine and American art, including outstanding works by Winslow Homer, Andrew Wyeth, and Edward Hopper. The 1983 I.M. Pei building is a modernist landmark in its own right.

Southern Maine Activities by Season

Summer (July-August): Peak season for beaches, sailing, whale watching, and the full range of outdoor and dining activities. Ogunquit Beach and Portland’s Old Port are at their most vibrant — and most crowded. Book accommodations well in advance for July and August.

Fall (September-October): Excellent shoulder season — beaches are quieter, restaurants are less crowded, and the weather remains good. Portland’s restaurant scene is actually better in fall when the summer tourist rush recedes. Foliage peaks inland in mid-October.

Winter: Portland is a genuine year-round city — excellent dining, the Portland Museum of Art, and First Friday Art Walk all operate through the winter. The beaches are beautiful in winter for walking. Skiing at Sunday River and Sugarloaf is within 2-3 hours.

Spring (May-June): The region comes alive in late May. Ogunquit’s Marginal Way is spectacular in June when beach roses bloom. Black flies are less of an issue on the coast than inland. Late June offers near-peak conditions with meaningfully lower crowds.

Getting Around Southern Maine

A car is essential for most of southern Maine. Portland is the exception — the city itself is very walkable and the Old Port, Arts District, and Eastern Promenade are all accessible on foot. The Amtrak Downeaster train connects Boston to Portland and Brunswick, with stops in Wells, Saco, and Old Orchard Beach — making Portland accessible without a car. US Route 1 connects the coastal communities from Kittery north through Ogunquit, the Kennebunks, and Portland, but summer traffic can be heavy. I-95/Maine Turnpike is faster for north-south travel between towns.

Southern Maine — Frequently Asked Questions

What towns are in Southern Maine?

Southern Maine generally refers to the region from Kittery at the New Hampshire border north through York, Wells, Ogunquit, Kennebunk, Kennebunkport, Saco, Old Orchard Beach, Portland, Freeport, and Brunswick. Portland is the region’s urban anchor and the state’s largest city.

What is Southern Maine known for?

Southern Maine is known for its beaches (Ogunquit Beach, Popham Beach), Portland’s nationally acclaimed food scene, the historic towns of Kennebunkport and Ogunquit, L.L. Bean in Freeport, lobster rolls, and easy access from Boston and the broader Northeast.

When is the best time to visit Southern Maine?

Late June and September offer the best combination of good weather, open businesses, and manageable crowds. July and August are the most popular months but also the most crowded and expensive. Portland is excellent year-round.

📌 Planning a Maine road trip? Read our complete One Week Maine Road Trip Itinerary — Portland to Bar Harbor with day-by-day stops, driving times, and insider tips.