Small Towns Near Portland, Maine
The best towns near Portland, Maine, for a day trip are Freeport, Ogunquit and Camden. Freeport has the L.L.Bean flagship, Ogunquit has the Marginal Way cliff walk, and Camden has the view from Mount Battie.
The ten towns below run nearest first, from an island 5 miles out in Casco Bay to Camden, about 65 miles away. Most are coastal and work as a day trip. Bethel and Camden are better as a weekend.
| Town | Distance | Best for |
|---|---|---|
| Chebeague Island, Maine | About 5 miles | a ferry ride, quiet island day |
| Freeport, Maine | About 15 miles | shopping, a rainy day |
| Kennebunkport, Maine | About 20 miles | beaches, strolling, trolleys |
| Bath, Maine | About 25 miles | maritime history, beaches |
| Boothbay Harbor, Maine | About 30 miles | gardens, harbor views |
| Ogunquit, Maine | About 35 miles | cliff walks, art, theater |
| Wiscasset, Maine | About 35 miles | lobster rolls, old houses |
| Portsmouth, New Hampshire | About 50 miles | history, dining, a walkable downtown |
| Bethel, Maine | About 60 miles | mountains, skiing, waterfalls |
| Camden, Maine | About 65 miles | harbor views, hiking, a weekend |
Distances are straight-line miles from downtown Portland, Maine, as the crow flies.
Chebeague Island, Maine
About 5 miles as the crow flies · Best for: a ferry ride, quiet island day
Great Chebeague is the largest island in Casco Bay with no bridge to the mainland. It was part of Cumberland until 2007, when it became its own town of about 400 year-round residents. It’s the easiest way to get a real island day from Portland.
Don’t miss: the Museum of Chebeague History in the old District 9 schoolhouse and the ferry ride itself
★ Good to know Casco Bay Lines runs from Portland, and the museum’s 2026 season ends October 12.
Freeport, Maine
About 15 miles as the crow flies · Best for: shopping, a rainy day
Leon Leonwood Bean opened his first store here in 1912, in the basement of his brother’s shop. Freeport is a town of about 8,700 in Cumberland County. L.L.Bean reopened its flagship in September 2026 after a $50 million renovation.
Don’t miss: the L.L.Bean flagship on Main Street, with its new trout pond, and the Desert of Maine, 20 acres of sand dunes in the woods
★ Good to know The Desert of Maine’s train rides run daily in July and August and on weekends in May, September and October.
Kennebunkport, Maine
About 20 miles as the crow flies · Best for: beaches, strolling, trolleys
Kennebunkport was first incorporated in 1653 as Cape Porpus. Today it’s a town of about 3,600 in York County. Walker’s Point, the Bush family’s summer estate, is here.
Don’t miss: Dock Square, Goose Rocks Beach and the Seashore Trolley Museum, which calls itself the first and largest electric railway museum in the world
★ Good to know The trolley museum is open Wednesday through Sunday until October 25, and Goose Rocks Beach needs a town parking permit.
Bath, Maine
About 25 miles as the crow flies · Best for: maritime history, beaches
Bath calls itself the City of Ships, and its yards launched about 5,000 vessels. Bath Iron Works, founded in 1884, still builds Navy warships. During World War II it launched a new ship about every 17 days.
Don’t miss: the Maine Maritime Museum’s 20-acre campus on the Kennebec River and Popham Beach State Park in nearby Phippsburg
★ Good to know At Popham, the sandbars to Fox Island flood about two hours after low tide, and the currents are strong. Swimming there is at your own risk after lifeguards finish in late August.
Boothbay Harbor, Maine
About 30 miles as the crow flies · Best for: gardens, harbor views
Boothbay Harbor is a harbor town of about 2,000 people in Lincoln County. Its footbridge crosses the inner harbor, and the 1956 film Carousel shot scenes here. The big draw sits just next door in Boothbay.
Don’t miss: Coastal Maine Botanical Gardens, New England’s largest botanical garden, known for its giant trolls
★ Good to know The gardens’ main season runs May to October, and Gardens Aglow lights them up from November 14 to January 2.
Ogunquit, Maine
About 35 miles as the crow flies · Best for: cliff walks, art, theater
Ogunquit split from Wells in 1980 and has about 1,600 residents. An art colony took root here after 1898. The 1.25-mile Marginal Way runs along the cliffs from Shore Road to Perkins Cove.
Don’t miss: the Marginal Way, the Ogunquit Museum of American Art and a show at the Ogunquit Playhouse
★ Good to know The art museum’s 2026 season ends November 1, and the Playhouse runs the John Mellencamp musical Small Town from October 1 to November 1.
Wiscasset, Maine
About 35 miles as the crow flies · Best for: lobster rolls, old houses
Wiscasset calls itself Maine’s Prettiest Village. It was the busiest seaport north of Boston until the Embargo of 1807. The Federal-era houses from those years still line the streets.
Don’t miss: Red’s Eats for a lobster roll and Castle Tucker, built by Judge Silas Lee in 1807
★ Good to know Red’s Eats closes for the season in mid-October, and Castle Tucker’s 2026 tours end October 11.
Portsmouth, New Hampshire
About 50 miles as the crow flies · Best for: history, dining, a walkable downtown
Portsmouth was settled in 1630 as Strawbery Banke, named for the wild strawberries on the riverbank. It’s a small city of about 22,000 on the Piscataqua River. It’s the one out-of-state pick on this list.
Don’t miss: Strawbery Banke Museum, with more than 350 years of history in the Puddle Dock neighborhood, and Prescott Park on the river
★ Good to know Strawbery Banke is open year-round and admission covers two consecutive days.
Bethel, Maine
About 60 miles as the crow flies · Best for: mountains, skiing, waterfalls
Bethel is a mountain town of about 2,500 in Oxford County and home to Gould Academy. It’s the base for Sunday River in neighboring Newry. In 2008 the town built a 122-foot snow woman named for Senator Olympia Snowe.
Don’t miss: Sunday River and Grafton Notch State Park, where a short path leads to 23-foot Screw Auger Falls
★ Good to know Grafton Notch’s main trailhead is about 14 miles north of Bethel on Route 26.
Camden, Maine
About 65 miles as the crow flies · Best for: harbor views, hiking, a weekend
Camden is a harbor town of about 5,200 in Knox County. Captain Frank Swift started its windjammer cruise fleet in 1936. Edna St. Vincent Millay wrote “Renascence” from atop Mount Battie.
Don’t miss: Camden Hills State Park, where you can drive or hike up Mount Battie for the view over the harbor
★ Good to know The Mount Battie Auto Road closes for the winter on December 1, or sooner if snow blocks it.
What’s the closest small town to Portland, Maine?
Chebeague Island is the closest, about 5 miles out in Casco Bay. On the mainland, Freeport is about 15 miles away as the crow flies.
What’s the best small-town weekend trip from Portland, Maine?
Camden is the pick for a weekend, with a harbor, a windjammer fleet and Mount Battie. Bethel is the mountain option, near Sunday River and Grafton Notch.
Which towns near Portland, Maine, are good for a beach day?
Kennebunkport has Goose Rocks Beach, and Ogunquit sits on the coast with the Marginal Way. Bath is close to Popham Beach State Park in Phippsburg.
Can you visit a Maine island from Portland without a car?
Yes. Casco Bay Lines ferries leave Portland for islands including Chebeague, Peaks and Long. Chebeague is its own town, with a small history museum.