Arriving at Logan airport in late afternoon, we drove through 9 miles of Boston surface streets during rush hour traffic before entering the freeway. Smooth driving after that to Portland where we stayed in the Old Port district.
Visiting Maine
May 9, 2026
Exploring the Historic Old Town Area of Portland, Maine.
We found Portland to be very accessible, easily walkable in the old town area. Portland’s Old Port district is the historic waterfront heart of Portland — a compact area of 19th-century brick warehouses, narrow cobblestone streets, fishing wharves, cafés, bookstores, breweries, galleries, and working docks along Casco Bay. The lighthouses just a short drive away were interesting. The lobster rolls we ate were good, though we learned to order them hot, as cold lobster on a roll seemed to have less flavor. Cold lobster is apparently the default, but for a small fee they will heat it.
on the drive to boothbay Harbor
boothbay harbor downtown
From Portland we took Highway 1, following the coastline to the small coastal town of Boothbay Harbor. The commuity is nestled at the end of the small harbor, on a rocky peninsula in midcoast Maine, known for its harbor filled with fishing boats, sailboats, lobster traps, and excursion vessels.
The town is compact and walkable, with wooden docks, inns, seafood shacks, galleries, ice cream stands, and weathered New England buildings facing the water.
I like how these areas catering to summer crowds are filled with older style inns, as opposed to motels and hotels.
Old, weathered structures often draw my attention — echoes of forgotten lives and vanished eras.
Visiting Camden and other towns
There were a number of small towns alog the coast we visited, Camden being particularly picturesque. We drove the road up Camden State Park for the views there. We were lucky to have the fog lift as we arrived.
Bar harbor and acadia national park
Downtown Bar Harbor is compact and walkable, with shops, cafés, galleries, and harbor views throughout. Compared with southern Maine towns like Kennebunkport, Bar Harbor feels wilder and more connected to Maine’s mountainous coast and northern Atlantic landscape.
Acadia National Park has a loop drive surrounding it, hugging the rugged coastline on its eastern and southern sides. We also drove the windy road to the top of Cadillac Mountain for amazing views of the larger area.
Kennebunkport
On our return to Boston, we stayed in Kennebunkport, the picturesque coastal town in southern Maine known for its rocky shoreline, historic sea captain homes, small harbor, and classic New England atmosphere. Originally a shipbuilding and fishing community, it later became a summer destination for wealthy families and visitors seeking Maine’s coast.
The center of town, especially around Dock Square, is filled with boutiques, galleries, seafood restaurants, inns, and cafés clustered beside the river and harbor.
We stayed in the Kennebunkport Inn, just a few steps from the harbor bridge and quaint old town. A small but nice community.
our driving route from boston
I was interested in learning about the original Wabanaki Native Americans in Maine, and while the Abbe Museum in Bar Harbor was not yet open for the season, I did pick up this book on the early history.
