Labor Day Fun in Portland, Maine

Looking for the best ways to spend Labor Day weekend in Portland, Maine? Whether you’re planning a relaxing escape, a family-friendly adventure, or something a little more lively, there’s plenty happening all weekend long. Here are some top events, activities, and ideas to make your Labor Day unforgettable — with direct links so you can plan ahead.

1. Portland Farmers’ Market – Saturday, August 30

Kick off your weekend with fresh Maine produce, local meats, artisan crafts, and live music. Perfect for grabbing goodies for a picnic or beach day.

Where: Deering Oaks Park
Portland Farmers’ Market

2. Labor Day Weekend Concerts at Thompson’s Point

Enjoy live music right on the waterfront! Bring your blanket, grab a local craft beer, and soak up the summer vibes.

Where: Thompson’s Point
Thompson’s Point Events

3. Casco Bay Labor Day Boat Cruises

Spend Labor Day exploring Portland’s beautiful coastline from the water. Choose from family-friendly sightseeing tours, island hops, or romantic sunset cruises. Keep your eyes peeled for seals!

Where: Casco Bay Lines Terminal
Casco Bay Lines

4. Animal Fun at Maine Wildlife Park

For something the whole family will love, visit Maine Wildlife Park to see moose, black bears, bald eagles, and more. A perfect way to mix education with outdoor fun.

Where: Gray, ME (25 min from Portland)
Maine Wildlife Park

5. Old Port Shopping & Dining

Wander through Portland’s historic Old Port, where cobblestone streets meet boutique shops, award-winning restaurants, and harbor views. Perfect for a casual day out or a romantic evening.

Where: Downtown Portland
Visit Old Port

6. Portland Museum of Art

Take in local and international art collections, featuring Maine artists and rotating exhibits. A great option if you want something relaxing and inspiring.

Where: 7 Congress Square
Portland Museum of Art

7. Picnic at Eastern Promenade

Pack up your goodies from the farmers’ market and head to Eastern Promenade for sweeping Casco Bay views. Stick around for the evening fireworks and enjoy Portland’s skyline under the stars.

Where: Eastern Promenade
Eastern Promenade Info

Make Your Labor Day Unforgettable

Labor Day in Portland, Maine, is all about enjoying the last sweet days of summer — from waterfront concerts to boat cruises, family-friendly wildlife adventures, and cozy picnics overlooking Casco Bay. Wherever you go, you’ll find plenty of ways to make memories.

Planning your Labor Day weekend? Share your favorite Portland spots in the comments — and don’t forget to check out our Box of Maine gifts to bring a little Maine magic home!

For even more Portland inspiration, explore our blog on Portland Travel: B&Bs and Airbnb Stays You’ll Love to plan the perfect long weekend getaway.