Columbus Day weekend in Maine marks the middle of the festival season, as well as the time when the foliage turns colors. Look forward to seeing trees abounding with vibrant red, yellow, and orange leaves everywhere you look. Book a stay at one of many Maine vacation rentals, whether you want to spend a day at a local fair, embark on a drive on a scenic byway, try your hand at fishing, or just sit back and relax as the summer winds down into fall. Discover the 11 best Columbus Day weekend getaways in Maine as you revel in the cooler weather, and get in one last hurrah before winter arrives.

Portland Head Lighthouse
Source: Flickr / Patrick Kinney

1. Cape Elizabeth

Cape Elizabeth sits just south of Portland, and a vacation rental here serves as a jumping-off point to historic landmarks, fantastic seafood, and oceanfront views. Discover the Portland Head Light, an 80-foot lighthouse, on the grounds of Fort Williams Park. The park offers picnic tables near the beach ideal for a waterfront lunch. Consider catching one of the boat excursions in Portland that take you past the lighthouse on the water. After a long day of outdoor frolicking, chow down at one of Portland’s many seafood restaurants to dine on local specialties, such as those found at Gilbert’s Chowder House and The Porthole.

Find vacation rentals in Cape Elizabeth

2. Bar Harbor

Bar Harbor lies next to Acadia National Park, which is perhaps the most scenic natural spot in Maine. Coves, inlets, rolling hills, rocky shores, and splashes of fall color bring Acadia National Park to life at this time of year. Hike up all seven peaks that eclipse 1,000 feet, explore some of the 158 miles of hiking trails, and take plenty of photos of the lovely fall colors. The best part about Acadia as this time of year is the lack of tourist crowds. When your adventuring is done, settle into your vacation rental and make your own seafood delight for dinner. On the southwest part of the island, stop by the Oktoberfest celebration.

Find vacation rentals in Bar Harbor

3. Newry

Newry hosts the Sunday River Fall Festival at one of Maine’s top-rated ski resorts. Practice your cornhole skills now, because you can win cash prizes for becoming the New England Cornhole Champion. If you’re strong, consider entering the annual North American Wife-Carrying Championship as you carry your lovely wife through an obstacle course filled with mud and logs. While you’re at the ski resort, take in the majestic views of the surrounding countryside. Grafton Notch State Park is a must-see as the waterfalls, peaks, and gorges create a unique natural landscape amid fall colors. Count on a rustic vacation rental here that takes advantage of the ever-present mountain views.

Find vacation rentals in Newry

Find the perfect Maine vacation rental on Tripping.com. Tripping.com is the world's #1 vacation rental search engine with over 10 million properties!

4. Boothbay Harbor

Ride the historic narrow-gauge railroad in Boothbay Harbor, and kick off autumn thanks to the Fall Foliage Festival over the entire three-day Columbus Day weekend. Peruse more than 60 antique cars while savoring local foods and viewing work by local artists. Just 15 minutes from Boothbay, check out the Damariscotta Pumpkinfest & Regatta as well as Freeport, both of which are part of Maine’s 40-mile Pumpkin Trail that celebrates the giant orange gourds in Maine. When you and your youngsters are tuckered out, head back to your cabin vacation rental and get a good night’s sleep.

Find vacation rentals in Boothbay Harbor

5. Fryeburg

The Fryeburg Fair lasts for eight days, including the Saturday and Sunday of Columbus Day weekend. Watch the grand parade on Saturday morning before ox pulling contests and harness racing take center stage. Sunday features a church service, a scooting contest with steers, and the grand sweepstakes for horse pulling. While here, take in the flower displays, wreath-making classes, and fair food that you know and love. There are plenty of fair rides for adults and kids alike.

Find vacation rentals near Fryeburg

6. Caribou

Visit the northeasternmost city in the United States when you head to Caribou, which lies just a few miles from the Canadian border. A gorgeous vacation rental here leads to more than 1,000 miles of trails to explore, including the Aroostook Valley Trail alongside the Bangor and Aroostook Trail. Four-wheel it with an ATV or glide around on two wheels with a bicycle while you breathe in the cool, fall air on trails normally reserved for snowmobiles and cross-country skiers in the winter. If you fancy another adventure, hop across the border into Canada to see Four Falls and its beautiful limestone bluffs.

Find vacation rentals near Caribou

7. Gardiner

Downtown Gardiner rings in the fall season with its Swine and Stein Oktoberfest. As the name implies, you can imbibe wonderful craft beers made in Maine, listen to live music, and feast on as many brats as you can stand. For a fun time, enter the frozen T-shirt race, the rock, paper, scissors championship, and the beard and mustache competition. Before you retire to your vacation rental for the weekend, you could be a three-time champion (and a local legend).

Find vacation rentals in Gardiner

8. Bangor

Bangor is a small city that has plenty to do. If you love horror fiction, pay respects at Stephen King’s mansion just outside of the downtown area; you can’t miss the spooky black gate adorned with wrought iron bats. Although you can’t get inside, just seeing the place is awesome. The Maine Forest and Logging Museum in nearby Bradley shows you exactly what logging was like in days gone by. The restored log-hauling railroad is a mechanical marvel that showcases the engineering prowess of traditional logging operations.

Find vacation rentals in Bangor

9. Weston

A vacation rental in Weston is your starting point for one of the most beautiful scenic drives in America. The drive along U.S. Highway 1, known as the Million Dollar View, takes your family on an 8-mile drive near three lakes, rolling hay fields, Mount Katahdin, and Peekaboo Mountain with New Brunswick, Canada, just a stone’s throw to the east. On a good day, you might find black bears, deer, eagles, loons, and moose. The Million Dollar View Scenic Overlook boasts three lakes to the east and mountains to the west in a gorgeous, 360-degree panorama.

Find vacation rentals near Weston

10. Kennebunk

A vacation rental in Weston is your starting point for one of the most beautiful scenic drives in America. The drive along U.S. Highway 1, known as the Million Dollar View, takes your family on an 8-mile drive near three lakes, rolling hay fields, Mount Katahdin, and Peekaboo Mountain with New Brunswick, Canada, just a stone’s throw to the east. On a good day, you might find black bears, deer, eagles, loons, and moose. The Million Dollar View Scenic Overlook boasts three lakes to the east and mountains to the west in a gorgeous, 360-degree panorama.

Find vacation rentals in Kennebunk

11. Winterville and Eagle Lake

Eagle Lake represents an outdoor paradise where you can truly get away from it all. Take a boat on the lake for a quiet fishing spot, or hike around the lake or ride an ATV when you want to view the fall foliage at a faster pace. Work your way up to Square Lake, Cross Lake, and Long Lake if one lake just doesn’t cut it (a waterway connects all of these lakes). Your rustic vacation rental with a full kitchen lets you cook whatever brook trout, lake trout, or landlocked salmon you catch during your fishing expedition.

Find vacation rentals near Winterville

 
Ready to go?  Check out these amazing Maine vacation rentals on Tripping.com.