Brewster House Bed & Breakfast

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  • Walking Distance to downtown Freeport
  • 3 course, gourmet breakfast served daily
  • All Rooms have private baths & luxury amenities
  • 24/7 Beer & Wine Honor Bar
Three people snowshoeing on a snowy day

Things to Do in Winter in Freeport Maine | A 3-Day Itinerary

Maine is a beautiful state for hiking, fishing, and water sports. But since you’ve found yourself here during the snowy season (lucky you!), here is an epic 3-day itinerary for the ultimate winter getaway. These are all the best things to do in winter in Freeport, Maine!


Day 1: Hang Out On Main Street

Before check-in at Brewster House Bed and Breakfast at 3 pm, we recommend checking out downtown Freeport. It is a mecca for great shopping and dining. Everyone can find a plethora of things to do in Freeport, Maine, in winter.

1. Shopping on Main Street

Peruse the hundreds of mom-and-pop shops, art galleries, and craft markets in and around downtown Freeport. Try something special at Sea Love, where you can make your own candles!

2. Lunch at Tuscan Brick Oven Bistro

Tuscan Brick Oven Bistro is one of the most popular restaurants in Freeport. Try its wood-fired steak, brick-oven pizza, homemade pasta, fresh seafood, craft cocktails, and more.

3. L.L. Bean Flagship Store

Walk off your big Italian meal in the L.L. Bean Flagship Store (nearly 220,000 sq ft). Stock up on all your winter essentials (flannels, cozy slippers, and all the outdoor gear you could ever need).

4. A Drink at a Brewery

Two of our favorites that we always recommend to our guests are Mast Landing Brewing Co. and Goodfire Brewing.

5. Dinner at Freeport Oyster Bar

Enjoy fresh oysters from local Maine farms and delicious beer, wine, and cocktails at Freeport Oyster Bar.

6. Watch a Live Show at Cadenza

Cap the night with a spectacular live show at Cadenza, a beautiful music center with performances all year.


Day 2: A Mountain Of Outdoor Adventure

After filling up on a hardy Brewster House breakfast, you’re ready for a fun-filled day of outdoor adventure. Snowshoeing, scenic sleigh rides, and farm-fresh food await you.

1. Rent Snowshoes

Pineland Farms has gear rental for cross-country skiing, snowshoeing, and sledding.

2. Lunch at South Freeport Village Market

The South Freeport Village Market offers delicious grab-n-go sandwiches/picnic fare to take on your upcoming outdoor adventures.

3. Scenic Sleigh Ride with Carousel Horse Farm

Stroll through quiet winter paths via horseback with Carousel Horse Farm, suitable for riders of all levels. Witness breathtaking views of the White Mountains, then enjoy hot cocoa, coffee, and home-baked desserts next to the fire.

4. Dinner at Jameson Tavern

Jameson Tavern has served locally sourced, authentic Maine cuisine in a cozy atmosphere since 1779!

5. Cap the Night with Wine and Beer at Brewster House

Brewster House is stocked up on unique wine and locally-made beer for you to enjoy after a long day of outdoor winter adventuring.


A lineup of five beer tastings

Day 3: Freeport Maine Good Eats

After check-out at 11 am, grab a bite before you hit the road. These are some must-see farms, breweries, and specialty food stores near Freeport. For all you foodies, these are some of the best things to do in Freeport, Maine, in winter.

1. Lunch at Isabella’s Café

Isabella’s Café serves hand-made baked goods, sandwiches, and salads, always made with locally sourced ingredients and lots of love.

2. Explore the Local Farms

Discover what local Maine farms are growing and producing. Enjoy house-made sandwiches at Pineland Farms and small-batch cheeses at Winter Hill Farm. The Winter Farmers Market in nearby Brunswick has dozens of local farm stands selling goods every Saturday, all winter long.

3. Beer Hopping at Local Breweries

There are many great local breweries around Freeport. Brickyard Hollow Brewing Company, Maine Beer Company, Goodfire Brewing , and Mast Landing Brewing are some of the best.

4. Dinner at Broad Arrow Tavern

Watch the talented chefs at Broad Arrow Tavern prepare your meal from their open-concept kitchen. Enjoy wood-fired pizza, grilled meat, salads, and the freshest seafood around. Relax outside by the wood burning fire pit after your meal and a favorite beverage.


More Fun Things To Do In Freeport, Maine, In Winter

The winter activities in Freeport, Maine, don’t stop there!

All Winter Long


Book Your Winter Getaway At Brewster House In Freeport, Maine!

From beer hopping to skiing to cheese tasting, there’s a plethora of great things to do in and around Freeport, Maine, in winter.

Brewster House Bed & Breakfast is the perfect place to rest after a huge day of winter adventuring. Our large rooms (with private baths, custom-made soaps, fine linens, fireplaces, and big bay windows) are ready for your arrival.

Enjoy unmatched comfort in an atmosphere of simple elegance. Check availability at Brewster House Bed & Breakfast and make your Freeport winter getaway an unforgettable one.

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