Labor Day Activities in Maine: 7 Fun Ideas

The arrival of Labor Day weekend signifies the end of another glorious summer and gives us one last opportunity to simply soak it all in. From exploring Portland’s cobbled streets (and seas!) to our final swims of the season, here are the best local Labor Day activities in Maine!

1. Explore Portland

There is no shortage of fun experiences to be had in charming Portland, Maine – at Cumberland Crossing, we feel very lucky to be located just a short drive from this lovely city!

Enjoy award-winning local restaurants, unique art museums and exhibits (Portland Museum of Art is a can’t miss stop), boutique shopping, sporting events, and much more! Walk the Eastern Trail throughout the city then treat yourself to some of the best craft beer in the country at Portland’s breweries; spend the morning shopping in the iconic Old Port then catch the ferry out to nearby Peaks Island for dinner with a view. Whatever you love to do, Portland is sure to have it!

2. Take a Hike

Labor Day weekend is the ideal time to get outside and go for a hike on one of the countless spectacular mountains and trails near Portland, Maine. Some of our favorite places to hike in the area include:

Chebeague & Cumberland Land Trust – Cumberland, ME
Mackworth Island – Falmouth, ME
Wolfe’s Neck Woods State Park – Freeport, ME
Blackstrap Hill Community Forest – Falmouth, ME
Hedgehog Mountain – Freeport, ME
Pleasant Hill Preserve – Scarborough, ME
Bradbury Mountain State Park – Pownal, ME

3. Road Trip to Bar Harbor

Home to Acadia National Park, Bar Harbor is one of the most picturesque places to visit in Maine and a wonderful long weekend trip! You could easily spend the entire weekend exploring Acadia: catch the sunrise at Cadillac Mountain, enjoy smooth bike riding along the Carriage Trails, and hike the Beehive Loop for unbeatable ocean views. Don’t forget to stop for a famous popover at Jordan Pond House! After exploring Acadia to your heart’s delight, check out downtown Bar Harbor for delicious seafood, boutique shopping and fun local bars!

4. Picnic at Portland Head Light

On a beautiful late summer day, there’s nowhere better to be than at Fort Williams Park – the home of the famous Portland Head Light. Fort Williams offers over 90 acres of lush, rolling lawn, historic bunkers, a small rocky beach, and coastal walking trails that take you throughout the park. It’s truly one of the most beautiful spots in Maine!

Don’t feel like packing your own picnic? Grab a fresh lobster roll from the Bite Into Maine food truck that’s parked on the property!

5. Go on a Bike Ride

Pack up your bike, fill up your water bottle and hit the trails for a delightful ride on one of Southern Maine’s many trails! In addition to the above hiking and walking trails, which are also bike friendly, some other biking favorites include:

Falmouth Community Park – Falmouth, ME
Jewell Falls Trail – Westbrook, ME
Mt. Blue State Park – Weld, ME
Mt. Agamenticus – York, ME
Saco Heath Preserve – Saco, ME
Coastal Maine Botanical Gardens – Boothbay, ME
Acadia National Park – Bar Harbor, ME

6. Sail the Casco Bay

Without a doubt, one of the best ways to spend a long weekend is by treating yourself to a chartered cruise on the Casco Bay with Sail Portland Maine! They offer two types of trips to choose from: a sail aboard traditional Friendship sloop Eleanor Hawkes for up to 6 guests or enjoy cocktail cruiser Calista Ann if you have a slightly larger party. Their cozy sails feel intimate and private, offering you a unique experience that you’re sure to remember for years to come. Admire Portland’s skyline, look out for the harbor’s wildlife and, if you can, catch the sunset!

Spots for Labor Day weekend are booking up quickly, so be sure to reserve your chartered cruise with Sail Portland Maine today!

7. Take a Late Summer Dip

In Maine, there is no shortage of crisp, cool bodies of water to choose from! For a refreshing dip on a warm end-of-summer day, you have countless choices between lakes, ponds and beaches. With over 6,000 freshwater lakes across the state and over 3,500 miles of ocean coastline, you have your pick!

Some of the best lakes in Maine include:

Sebago Lake – Casco, ME
Lower Range Pond – Poland, ME
Echo Lake – Mount Desert, ME
Flagstaff Lake – Stratton, ME
Rangeley Lake – Rangeley, ME
Moosehead Lake – Greenville, ME
Webb Lake – Weld, ME

Some of the best beaches in Maine include:

Crescent Beach – Cape Elizabeth, ME
Scarborough Beach – Scarborough, ME
Higgins Beach – Scarborough, ME
Pine Point Beach – Scarborough, ME
Old Orchard Beach – Old Orchard, ME
Popham Beach – Phippsburg, ME

Cumberland Crossing by OceanView

There is truly nothing like Maine independent living for seniors! From pristine beaches to breathtaking mountains, enjoy all the wonderful advantages of retiring in our beautiful state.

Cumberland Crossing by OceanView offers two spacious, customizable cottage floor plans to choose from, designed to fit your style and needs. Our unique 100% refundable entrance fee and inclusive monthly maintenance fee ensures that you can enjoy your hard-earned retirement years doing what you love most!

To learn more about our active retirement community, please contact us at Cumberland Crossing today!