Day Trip: The Best Fall Drives Near Boothbay Harbor

Your upcoming autumn escape to breathtaking Linekin Bay Resort in Boothbay Harbor is fast approaching. Whether you’re planning on visiting Midcoast Maine for an elegant fall wedding, a relaxing sailing voyage or a leaf-peeping and hiking adventure, our back roads in Autumn are surrounded by beautiful and colorful foliage. Choosing a resort in Boothbay Harbor is simple, Linekin Bay Resort has newly renovated camp-style cabins and lodges, oceanfront accommodations, restaurant and bar on-site, plenty of activities for all ages, and stunning bay views. The hard part is deciding which routes to tour on your memorable autumn drive. Luckily for you, we have personally handpicked three of the best fall drives in all of Midcoast Maine.

Woolwich to Five Islands

Hop on Route 127 in Woolwich, which rests across the Kennebec River from the city of Bath, and start heading south en route to Five Islands. This route crosses the Sasanoa River twice as it meanders past stunning island forestry. Doubling Point Lighthouse is one-mile off Route 127. This picturesque 23-foot tall lighthouse was built in 1898 and is still used today! Don’t be afraid to walk out to the light, which overlooks the scenic and colorful Kennebec River.

Your journey continues southward through Arrowsic and Georgetown before arriving in breathtaking Five Islands. Every mile of this 18-minute drive is speckled with stunning foliage, active wildlife, and eventually sweeping Sheepscot River views. Reid State Park is a short detour if you wish to have a picnic on the beach; otherwise, Five Islands Lobster Co., one of the most beloved seafood joints in Maine, has fresh lobster, clams, and mussels.

Wiscasset to North Whitefield

The scenic and relaxing northbound countryside drive from lively Wiscasset to the tiny town of North Whitefield near Clary Lake is a genuine hidden gem. The journey takes less than an hour round-trip, but the simplicity and seclusion of Route 218 make it an absolute must for any autumn day trip. You’ll get quick glimpses of the Sheepscot River on nearly a dozen occasions.

The ultimate diversion on this journey should be the Sheepscot General Store and Farm in Whitefield. Stop in for a slice of delicious cherry pie and perhaps a bottle of fine wine, which can be opened at sunset on the sundeck at Linekin Bay Resort. Route 218 meanders through the quaint villages of Alna, Head Tide, and Whitefield, all of which have unique stories and inviting shops, dining, and landmarks. The unfeigned delight of this drive is the majestic blend of fall foliage, red barns, and foggy Sheepscot River bends.

Bath to Brunswick

The beautiful 31-mile drive from Boothbay Harbor to Brunswick is one of the best in Midcoast Maine. We’re going to focus on the beautiful eight-mile stretch on US-1 from Bath to Brunswick. On the surface, driving on a highway shouldn’t be overly spectacular, but this stretch is a splendid, colorful trip.

There are glimpses of the breathtaking Androscoggin River, which snakes around the north side of Brunswick. You also have a terrific vantage point of the island chains to the south and the mountains to the north. Stop at the Androscoggin Swinging Bridge for spectacular fall foliage before heading to Flight Deck Brewing for a pint on their spacious patio. On the way back to Boothbay Harbor, make a detour in Wiscasset for the best lobster roll in the world at Red’s Eats.

The Best of Boothbay Harbor

Head back to your cozy waterfront cabin after a memorable afternoon of foliage, lobster, and pie. Prepare for a night of fine dining at the Deck Bar & Grill, a beautiful Linekin Bay sunset, all while sitting fireside. The Boothbay Food & Music Festival is fast approaching – remember to make a reservation at Linekin Bay Resort before it’s too late!