How to Spend One Winter Day in Freeport Maine

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If you’re planning a trip to Maine, you may want to consider a day exploring Freeport. 

Freeport is a tiny town just 20 minutes north of Portland. It has a great walkable downtown and plenty to eat and see. 

My husband and I both grew up close to Freeport and spent many days exploring the area. The downtown has really expanded over the years and has never offered more to visitors. 

Most famously, the LL Bean headquarters are stationed in Freeport, along with both local and outlet shopping, and plenty of restaurants to keep you full. 

To help you on your visit to Freeport, I’ve created a one-day itinerary for you based on a recent visit we had in winter. 

Downtown Freeport, Maine in March

Why Should You Visit Freeport, ME in Winter?

Great question! Firstly, it helps you avoid the crazy crowds of summer in Maine. 

Freeport can get pretty busy during the summer. Located on Route 1, many tourists drive through Freeport if they are seeking the scenic route from Portland to Camden or Bar Harbor. So, naturally the downtown can get a bit congested. 

In addition, wintertime in Freeport offers a more relaxing feel to the small town. The ambience of fresh snow and holiday lights make it even more appealing to visitors. 

And finally, wintertime in Freeport offers a unique way to view the surrounding natural beauty. While most visitors will enjoy the rocky coastline via hiking and kayaking, you’ll get the chance to experience nature via snowshoeing or cross-country skiing. And did I mention no crowds? Seriously, you’ll have the area virtually to yourself. 

Read More: 4 Reasons Maine Should Be Your Next Vacation Spot

Freeport is a Perfect Day Trip from Portland, Maine

If you are visiting from Portland, you’ll be surprised how close Freeport is to Portland, yet it feels like you’re hours away from the “city”. You may not consider Portland a city, but we do in Maine!

To visit from Portland, you’ll most likely want to rent a car.

Read More: 6 Fantastic Day Trips from Portland You’ll Love

Start your day of fun in Freeport, ME!

A note, this itinerary may require snowshoes and proper winter boots, depending on snow levels when you’re visiting. If you are in need of rentals, you may want to head over to Pineland Farms in New Gloucester, only 20 minutes from Freeport. 
Pineland farms offers snowshoe and cross-country skiing rentals as well as an extensive trail system, perfect for beginners or those who don’t have their own! They also have a wonderful market where you can enjoy lunch after burning all those calories!

These are the winter boots I swear by! I wear these boots all four seasons! They are perfect for winter adventures, rainy days, muddy walks, and cold days. Seriously, the best winter purchase I’ve ever made.

Sunrise at Winslow Memorial Park

Winslow Park is a wonderful hidden gem in this area. In the warmer months, the park features a beach, playground, and multiple picnic area rentals, along with a large campground. 

The campground is open from late May to October. There are over 100 campsites offering both tent and RV sites, but there aren’t any RV hook-ups. 

Dogs are allowed in the park, but not on the beach or playground. 

If you’re just visiting for the day, there is a charge during the summer months, $3 per person.

Winslow Park in the winter is a totally different place! It’s serene and quiet, offering the most relaxing way to start your morning. 

Snowshoes aren’t totally necessary to enjoy the sunrise, it just depends how much snow Freeport has gotten recently. The road into the park is paved so you could easily enjoy the sunrise from the road as well. 

Sunrise at Winslow Memorial Park in Freeport, Maine

Breakfast at Sunrise Cafe

There are a few options for breakfast in Freeport. 

We love Sunrise Cafe the most because of the great tasting food and local small town feel. You have to try their homemade corned beef hash, a Maine favorite!

You can also try Freeport Cafe, Isabella’s Cafe, or Coffee by Design located in LL Bean. 

Exploring Downtown Freeport, Maine

If you like shopping, you’ll really enjoy downtown Freeport and the Freeport Village Station. 

You’ll find LL Bean, Patagonia, Ann Taylor Loft, J Crew, and more. 

*LL Bean has multiple stores spread over downtown Freeport. Below you’ll see the Bike, Boat, and Ski store is just one of their buildings.

And don’t forget to check out the LL Bean outlet store in the Freeport Village Station

There are also numerous local shops which I try to support as much as I can!

Check out Haberdashery, Rustic Arrow, Sherman’s Maine Coast Book Shop, Wicked Whoopies, Leapin Lizards, and more. 

There’s a ton of parking in downtown Freeport, but the earlier you can get there the better as it does fill up fast in the summer months.

LL Bean in Freeport, Maine

Lunch at Antonias Pizzeria Bar and Grill

This local pizzeria has been in Freeport since 2007 and serves the best pizza in town. We love their Buffalo Chicken and Broccoli pizza! 

They also have a great patio for the summer months. 

Afternoon Walk or Snowshoe at Wolfe’s Neck Woods State Park

I’ve been to Wolfe’s Neck State Park numerous times, and I always love coming back. It’s got plenty of parking and is conveniently located just minutes from downtown Freeport. 

Read More: The Best State Parks in Maine: A Local’s Opinion

During the winter tha gate park will be closed so park alongside the road, making sure not to block the gate. 

There is a series of trails perfect for a light hike or snowshoeing in the winter. Again, if you’re in need of rentals you may want to skip Wolfe’s Neck State Park and instead head over to Pineland Farms in New Gloucester where you can rent snowshoes and cross-country skis. 

The state park also features tent and RV camping in the summer as well as a Nature Center.

Wolfe’s Neck Woods State Park, Freeport, ME

Dinner at Tuscan Brick Oven Bistro

This is my favorite restaurant in Freeport. I love their relaxing and laid back atmosphere and I always have a great time while I’m there. 

You have to try their charcuterie board! They also have a great selection of wine. 

You’ll definitely want to make a reservation if you’re visiting for dinner. 

Dessert From Wicked Whoopie

While you’re exploring downtown Freeport, stop by Wicked Whoopie. Pick up a few treats for after dinner! Trust us, you’ll want to try these classic Maine desserts. You might have trouble choosing a flavor from red velvet to chocolate chip and gingerbread to the classic chocolate. 

Wicked Whoopies started in Gardiner, ME and now ships their delicious treats all over the US. So, you can enjoy more whoopie pies when you’re back home!

Other Ways to Enjoy Freeport, Maine

If you’re still looking for ways to get active you can check out Audubon Mast Landing Sanctuary, Hedgehog Mountain, and Bliss Woods Preserve.

If you’re planning a trip in December, LL Bean goes all out with decorations and holiday light displays. They even have a skating rink with rentals available, and a free hot chocolate area. 

Final Thoughts

As you can see, just one day in Freeport isn’t enough but this itinerary is a great start to a visit. 

I hope you enjoy your time visiting Freeport, no matter the time of year!