History and Harbors

Discover Maine’s Heritage and Scenery: A Summer Feet 6-Day Walking Tour

Maine, first explored by Europeans in the early 1500s, is steeped in a rich and diverse history. Our 6-day easy walking tour is designed to give you a comprehensive insight into Maine’s captivating past, its distinctive architecture, and its breathtaking natural beauty. This tour begins in the charming city of Portland, known for its well-preserved historical buildings and vibrant cultural scene. As you stroll through the city, you’ll witness a blend of historic and modern architecture alongside picturesque waterfront views. Next, the tour takes you to the heart of Maine’s mid-coast, an area celebrated for its quintessential New England beauty. Here, you’ll explore quaint coastal towns, each brimming with character and stories that echo Maine’s maritime heritage. The tour’s highlight is undoubtedly the stunning Acadia National Park, an area of matchless natural beauty. You’ll be treated to panoramic views of rugged coastlines, pristine forests, and serene mountain landscapes. The park’s beauty showcases the untouched side of Maine, making it a perfect finale for your 6-day exploration.

Join us on this walking tour to experience the unique charm, rich history, and natural splendor of Maine, from Portland’s bustling streets to Acadia’s tranquil trails. If you have any questions, please get in touch.

(Want to explore more multi-day New England tour options? Check out our Cycling Trips in Maine.)

Highlights

Pricing

Tour Price: $3595 per person double occupancy

Single Supplement: $900

2025 Dates

September 21-26
October 12-17

Pickup/Drop Off

Portland, Maine (PWM)

Itinerary

DAY 1 Discover Portland

Meet your guides in the early afternoon in Portland. Founded in 1623 and full of charm, you and your group will enjoy a guided walk through Portland’s historic West End and a visit to the Portland Head Light before our welcome dinner.

Walking: 1-2 miles
Meals: Dinner
Lodging: The Portland Regency

DAY 2 Freeport, Damariscotta, and Pemaquid Point

Known as the home of L.L. Bean, Freeport is much more than shopping! Today we enjoy an easy stroll through the woods and along the shore of Wolfe’s Neck State Park. After a short drive, we pause for you to enjoy lunch on your own and to explore the town of Damariscotta before an afternoon walk through the Dodge Point Preserve. Here we follow old farm roads through mixed forests to the shore of the Damariscotta River. Our path along the river offers a great opportunity to spot a variety of shorebirds. A short drive takes us to the Pemaquid Point Lighthouse where we enjoy wine and cheese overlooking the ocean.

Walking: 4 miles
Meals: Breakfast and Dinner
Lodging: The Bradley Inn

DAY 3 Owls Head Light and the Rockland Breakwater

In the morning you visit the Owl’s Head Light before walking the mile-long breakwater in Rockland Harbor for great views of Penobscot Bay and Rockland Harbor. After a morning spent exploring Rockland and enjoying lunch, it is time for a short drive to Camden where the group will enjoy a sail on an antique wooden schooner.

Walking: 3 miles
Meals: Breakfast & Lunch
Lodging: The Hartstone Inn

DAY 4 Camden Hills and Castine

Your morning begins with a hike in Camden Hills State Park for views of Lake Megunitcook, Penobscot Bay, and the opportunity to see the sweeping panorama of the Maine Coast all the way to Acadia National Park. In the afternoon we visit Castine, one of the most historic towns in Maine. Castine has flown the flag of four nations in its rich history. Enjoy a walking tour of the town and the monuments to early struggles for control of the new world.

Walking: 5 miles
Meals: Breakfast, Lunch, and Dinner
Lodging: The Castine Inn

DAY 5 Schoodic Head

Today you travel to the quiet part of Acadia National Park: the Schoodic Peninsula. Hike the Buck Cove Mountain Trail for wonderful views of the ocean and Acadia National Park.

Hiking: 4 miles
Meals Breakfast, Lunch, and Dinner
Lodging: The Harborside Hotel

DAY 6 Cadillac Mountain

The highest peak on the Eastern Seaboard between Maine and Rio de Janeiro, Cadillac is the first place in the United States to see the sunrise. We will drop you where the trail crosses the Park Loop Road so you can walk the last mile to the summit. Enjoy views of Frenchman Bay and the Porcupine Islands. A noon departure takes you back to Portland.

Hiking: 1 mile
Meals: Breakfast

What's Included

Five nights’ lodging
4 Dinners, 3 Lunches, 5 Breakfasts
Hotel, Meal and Activity Gratuities
Experienced Leaders
Van Transport
Snacks and Beverages

National and State Park Entry Fees
Souvenir Water Bottle and T-Shirt (available in men's and women's fit)

Views were amazing. Guides were friendly and personable. Lobster roll was delicious. I upgraded to the ebike (first time riding one) and 10/10 recommend it. I wasn’t looking for a workout. Just wanted to see the sights and enjoy myself. Portland was my favorite stop from a New England cruise.

Five Stars to Rick (our guide) and the folks at Summer Feet Cycling. The ride was perfectly tailored to our group of nine middle aged individuals. The sights were terrific and the lobster role for lunch was the best I have ever eaten. Thanks for making our time in Maine a memorable experience.

Our Summer Feet cycle along the Maine coast was glorious. In early September, we had perfect weather. We cycled along breathtaking views. Then we caught our breath in quaint Maine towns and fishing villages. Each evening our luggage was waiting for us at a charming inn, where we were served breakfast before heading out the next morning. The Summer Feet staff were friendly and efficient. We will hope to plan another Summer Feet trip soon! Pedal The Coast

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