Labor Day Weekend in Maine

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Advisor - Allison Biggs
Curated By

Allison Biggs

  • Maine

  • Adventure Travel

  • Family Travel

  • Nature Escapes

  • Road Trip Travel

  • Summer

  • Coastal

  • Foodie

  • Sightseeing

  • Relaxation

Portland Head Light, Maine's oldest lighthouse, stands majestically on the rugged cliffs of Cape Elizabeth.
Curator’s statement

There’s nothing quite like New England in late summer. The weather begins to shift toward a crispness, and the crowds of city weekenders are starting to thin out. Labor Day Weekend, often considered the last true weekend of summer, is an ideal time to explore coastal Maine. In just three days, you can sightsee in Portland and Bar Harbor, satisfy your cravings for lobster and unwind in the serene atmosphere of New England life.

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Where to stay in Maine

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Things to do in Maine

Jordan Pond is a crystal-clear glacial lake located in Acadia National Park, Maine.
  • Lighthouses galore:
    Maine is synonymous with lighthouses. You can find several around Portland and Bar Harbor and on your way from Portland to Bar Harbor. The most iconic is the Portland Head Light House.

  • Whale watching:
    Not for the faint of heart (or stomach) but absolutely worth it. You can spot humpbacks and fin whales, porpoises and puffins and a variety of other marine life. Be sure to dress warmly – the temps drop on the open water and you're likely to get a little wet if you sit outside (which, trust me, you should). There are plenty of places to buy dramamine for the motion sickness inclined.

  • Hiking in Acadia National Park:
    Acadia is a glorious park to visit in the late summer. The crowds are light, giving you ample time and space to wander Jordan Pond, the Bubbles and Cadillac Mountain. It's also very easily drivable with plenty of overlooks to stop at along your way.

  • Sailing:
    Take a look at Acadia or Portland from a different perspective. This area is prime for sailboats. Enjoy one at sunset for an especially romantic setting.

  • Bar hopping:
    Portland has a great scene of local dives a block or two back from the tourist strip. Enjoy the local ambiance and cheap beverages in downtown before retiring back to your hotel.

  • Stroll through quaint towns:
    Bar Harbor is quintessentially quaint, as are several small towns you'll drive past on your way from Portland to Bar Harbor. Break up the drive with a stop here and there to get a real feel for Downeast.

  • Rent e-bikes:
    E-bikes are great for exploring the hilly area around Bar Harbor. You can even take them into the park for a unique ride through nature.

  • Enjoy the pool:
    This may sound strange given the altitude, but if the sun is still shining during Labor Day Weekend you may find yourself in need of a cool dip. The Bar Harbor Inn & Spa has a prime location on Bar Harbor's coast, and an infinity pool looking out over the water to boot.

Places to eat & drink in Maine

The recommended blueberry ice cream in Maine at Jordan Pond Ice Cream & Fudge.
  • Portland Lobster Company:
    Located on a dock overlooking the Portland Bay, you can eat fresh lobster rolls, plates, soups and a lot more unique lobster combinations, while watching boats bring in their catches of the day.

  • Dock Fore:
    Portland does a lot of things really well – one of them is the dive bar. This place slings up cheap drafts and cocktails (especially during happy hour) and greasy eats. The vibe is local and grungy.

  • Holy Donut:
    One must visit one of the Holy Donut locations while in Portland. If you love donuts, go. If you don't love donuts, GO. They're made of Maine potatoes and come in a variety of flavors, from the basic cinnamon sugar to the zany everything cannoli. Real ones know the blueberry donut is supreme.

  • Side Street Cafe:
    Located on a side street (duh) in Bar Harbor, this place makes great sandwiches. It's a little off the beaten path, which means you get away from the crowds of tourists on the main strip.

  • Royal Indian:
    Two buildings down from the aforementioned Side Street, Royal Indian is some of the best, authentic Indian food you will ever have. The warm spices especially hit the spot on a chilly Maine evening.

  • Rosalie's Pizza:
    This place is constantly slammed, but you move through the line quickly and get your slices even quicker. Order by the slice – they're massive and cheap.

  • Jordan Pond Ice Cream:
    Bar Harbor is lousy with ice cream shops – at all hours of the day, you'll find people wandering around, cone in hand. This place is the best, with large scoops and endless flavors. I highly recommend the blueberry – when in Maine, right?

Advisor - Allison Biggs

Travel Advisor

Allison Biggs

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This guide is part of our ongoing series on travel to Maine. Looking for more travel inspiration? Check out my guide, How to Spend a Long Weekend at the Fontainebleau Miami Beach.

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