Portland, Maine with the Family: Surfing, Outlets, and Labor Day Rides

Portland, Maine with family, it's the perfect kind of getaway for a long weekend: a few hours' drive from Quebec, an easy-to-visit coastal city, good food spots, and enough activities to please both teens and parents. To wrap up the summer, we spent three days in Maine, including a stroll through Portland, surfing in the icy water, outlet shopping, amusement rides at Old Orchard Beach, and steamy clam chowder by the sea.

For several years now, we've had a little tradition: taking advantage of Labor Day weekend to head to Maine. This time again, we chose a simple and effective formula: 3 days / 3 nights, with Portland as our base to explore the coast, enjoy the maritime atmosphere, and end the summer on a truly exotic note.

We arrive Friday evening, we settle in quietly… and the adventure begins the very next morning.

Day 1 — Discovering Portland, Maine with the family

For this first day, we've chosen to discover Portland, Maine with family on foot. It's a human-sized city, pleasant and easy to explore: we To start our weekend in Portland, Maine with family, We'll dedicate the day to exploring downtown. Portland is an easy city to visit with teenagers: the downtown area is compact, pleasant to walk around, and lively enough that you'll never be bored.

We start by strolling through the downtown streets, between the shops, the cafes, and the area near the water. The maritime atmosphere is everywhere, and that's exactly what we're looking for to get into vacation mode on the very first day.

For a first visit to Portland with family, Here are three stops that we particularly enjoyed:

• Victoria Mansion, for its historical and spectacular aspect; ;
• Portland Observatory, for the panoramic view; ;
• Casco Bay, for a beautiful walk by the water.

It's a simple, yet perfect day to take the city's pulse. If you're wondering What to do with the family in Portland, Maine, in our opinion, this is an excellent way to start: a bit of history, a nice walk, and just enough activities to enjoy without rushing.

Day 2 — Scarborough Beach, surfing, and Old Orchard Beach with the family

In the morning, we're going surfing at Scarborough Beach, one of our favorite stops for enjoying the coast near Portland. Maine water is cold, even in late summer, but the kids love the experience. Between the waves, the drops, and the laughter, this is the kind of activity that really makes a family trip memorable.

In the afternoon, we continue with Old Orchard Beach with the family, a must-do during a weekend in Southern Maine. Between the stroll on the pier, the rides, and the arcades, the atmosphere is festive, lively, and perfect for teenagers. The only danger: the arcades can easily blow the budget if you don't set a small limit.

Day 3 — Last stops before returning

For our last morning, we're making a stop at Cabela's, still popular with children, before continuing towards Freeport Village Station, about 25 minutes from Portland. It's one of the best places to shop in the area, with stores like L.L.Bean, Nike, Old Navy and Gap Kids, especially interesting during the Labor Day sales.

We'll then get back on the road towards Quebec in the mid-afternoon. This timing works well for us: it allows us to enjoy a bit more of Maine while avoiding ending the weekend in traffic.

Our favorites

• Surfing at Scarborough Beach—cold, but memorable
• Downtown donuts — a must
• Old Orchard Beach — The perfect blend of fun and nostalgia
• Portland's Microbreweries — A Truly Solid Scene

What we would do again (or not)

✅ We would redo:

• The mix of city + beach + rides
• The detour to Old Orchard Beach
• Going to Cabela's with the kids

We would do it differently:

• Better budget oversight for arcades
• Book very early for Labor Day (prices go up fast)