Local tips, Suggestions, and Destinations to Create Family Fun in Greater Portland

Winter in Portland can be really beautiful, and it can also be the time of year when you’re looking for a little inspiration on what to do.

Whether you’re getting outside for some fresh air or leaning into something warm and cozy, there are plenty of easy, family-friendly ways to build a weekend that feels fun without being overwhelming. From exploring the waterfront and hopping on a ferry to heading just outside the city to places like Freeport and Yarmouth, the Greater Portland region makes it easy to mix outdoor adventure with good food and relaxed stops along the way.

In this two-day itinerary, you’ll find a mix of simple outdoor activities, cozy places to warm up, and a few easy stops that come together to create a well-paced winter weekend.

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Day One

Start the day with hot chocolate at Coffee By Design in Portland. Their Diamond Street location is welcoming, and you can peek at their roastery while you order your coffee. It’s a great way to warm up before heading out, and during the winter, they offer a rotating menu of seasonal drinks that make the stop feel extra cozy. Options like a cardamom bun latte, maple matcha, or a hazelnut praline latte add a fun twist and make it easy to lean into the season right from the start.

Local Tip: Their cream cheese brownies are the best, and big enough for sharing.

From there, head to Casco Bay Lines for the Mailboat Run. Casco Bay Lines operates 365 days a year, serving as a true lifeline to the islands, not just a scenic cruise. The Mailboat Run is a working boat that delivers mail, freight, and supplies to several islands while also carrying passengers, which makes the experience feel both authentic and memorable. The route stops at multiple islands, giving you a glimpse into everyday island life. It’s been running in some form since the 1870s, making it the longest-running mailboat service in the country.

A ferry ride is a really fun and easy way to experience Casco Bay in any season. You can stay inside or head out on deck if the weather is nice. On a clear day, you’ll see lighthouses, historic forts, lobster boats, and seabirds, along with views of the different islands in the bay. It’s a nice mix of activity and sightseeing without needing to plan too much.

Local Tip: Not enough time for the mailboat run? You can choose a single island trip for a shorter version of the mailboat run. Don’t forget that some locals use the ferry to go to and from work, school, and more.

After returning to land, it’s easy to spend some time exploring Portland’s Old Port and nearby neighborhoods. The ferry terminal is right in the heart of downtown, so you can walk to shops, cafés, and local spots without needing to drive.

Local tip: Missing a furry friend at home? Stop by Fish & Bone on India Street to pick up a giant lobster stuffy, locally made dog treats, or some catnip pouches to bring home.

Next, head over to Thompson’s Point for ice skating. The rink is large and great for all skill levels, and there’s a warming hut with hot chocolate and both alcoholic and non-alcoholic drinks. There are also restrooms on site, and depending on the day, food may be available. One unexpected highlight is watching planes come in for landing at the nearby jetport while skating, which kids especially tend to love. It’s also worth checking their event calendar ahead of time, as they often host themed skate nights and special events, like Taylor Swift night and other fun seasonal happenings.

If you’re looking for an indoor option or want to mix things up, the Children’s Museum & Theatre of Maine is next door and a great stop for younger kids, with interactive exhibits and plenty of space to play and warm up.

In the afternoon, make your way up to Freeport for lunch at Mast Landing Brewing Company. The brewery is spacious and easy to access, with plenty of parking. In addition to their outstanding beer, they offer canned cocktails, mocktails, soda, and warm drinks like hot toddies and hot chocolate in the winter.

End the day with some fresh air at Wolfe’s Neck Woods State Park. The park has a mix of wooded trails and shoreline paths along Casco Bay, making it a great spot for snowshoeing or cross-country skiing. In the late afternoon, the light is especially nice, and it’s often quiet enough to feel like you have the trails to yourself.

Afterward, head to Gather in Yarmouth for dinner. It’s a warm, welcoming spot that works well for families and is an easy stop on the way back toward Portland after a day of being outside.

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Day Two

Start the day at Rosemont Market & Bakery. It’s a great stop to pick up breakfast and coffee, along with some grab-and-go items for later.

Local Tip: Their prepared meals are perfect to take home or save for another night, making it an easy and practical stop to start the day.

From there, head over to Fort Williams Park in Cape Elizabeth. Visiting in the winter feels especially magical, whether you catch it during a light snow or a clear, crisp morning. You can walk out to see Portland Head Light, take in the ocean views, or find one of the hills for sledding. It’s one of the best spots in the area for it, with wide open space and beautiful coastal scenery.

Afterward, make your way up to Freeport and stop at Maine Beer Company. Known for its strong commitment to sustainability, the brewery is a Certified B Corporation and focuses heavily on environmental responsibility. It’s a bright, welcoming space with excellent pizza and a wide range of beers, making it a great midday stop to warm up and relax.

While in Freeport, take some time to explore the shopping area. A stop at Wilbur’s of Maine Chocolate Confections is especially fun, where you can browse, sample chocolates, and even catch a glimpse of the production process. Make sure to check out their calendar online to see what events may be happening that day.

Local Tip: If the kids need to burn off some energy, Winslow Park is a great nearby stop, with a large pirate ship playground and open space to run around before heading to the next destination.

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