Friday
Beer, Italian comfort food, and stylish stays

Start your visit to Freeport in the expansive tasting room at Maine Beer Company. With 20 taps from the craft-beer favorite, there is sure to be something you’ll like. Last year the brewery unveiled a new, much larger tasting room, which has a wood-fired pizza oven and a bronze tree fountain sculpture.

If you want more options than the pizza and salad at the brewery, continue on to Tuscan Brick Oven Bistro. The Italian restaurant has house-made pasta, brick-oven pizza, sandwiches, and more, and is perfect for families and large groups.

The best accommodations in town are found at Harraseeket Inn, which boasts 94 rooms with luxurious touches, some including a fireplace and Jacuzzi tub. The inn also has a guest house furnished with products from the L.L.Bean Home Store and a few special rooms appointed by furniture makers with showrooms in Freeport: Thos. Moser and Chilton Furniture.

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Saturday Morning
Main Street shopping and outdoor adventures

Avoid some of the shopping crowd by hitting Main Street early. While online shopping has taken some of the deal-seeking fun out of perusing the outlet racks, there’s still a thrill in making great finds at name-brand stores like Nike, Polo Ralph Lauren, Brooks Brothers, and Coach. However, the more interesting shopping is at locally owned shops.

A longtime Freeport favorite, Brown Goldsmiths, just off Main Street on Mechanic Street, sells fine jewelry and designs and makes custom pieces. Another local shop, Rustic Arrow, stocks a curated collection of women’s clothing and accessories and playful and trendy home goods, with a focus on female designers and socially conscious brands. While Sea Bags now has more than two dozen retail stores across the country, including Freeport’s Bow Street, the company is headquartered on Portland’s waterfront, where it designs and manufactures its bags and accessories out of recycled sails. No trip to Freeport is complete without stopping at the ultimate global-yet-local retailer: L.L.Bean. The flagship store, which, apart from the recent coronavirus-related shutdown, is open 24 hours, 365 days a year, has no shortage of square footage to explore (including fish ponds!), but the L.L.Bean Outlet Store is also worth visiting.

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If the weather is cooperating, opt for a picnic lunch. Bow Street Market has all the provisions you’ll need, including sandwiches, salads, prepared food, and a well-curated wine and beer selection. After picking up supplies, keep on driving to one of our favorite places for a picnic lunch, Wolfe’s Neck Woods State Park. The park has plenty of picnic tables as well as wooded walking trails along the rocky coastline.

If you want more lively recreation than gentle coastal walks, book a session with the L.L.Bean Outdoor Discovery Programs. You can learn a variety of activities, including paddlesports, fly casting, archery, and sport shooting. Families with kids interested in animals will love Wolfe’s Neck Center for Agriculture and the Environment. The nonprofit organization on 600 acres of coastal land has educational and recreational activities for people of all ages, including farm tours and private goat hikes.

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If you prefer hard cider to hayrides, venture just west of Freeport to Portersfield Cider in Pownal. The small-batch operation specializes in ciders made from heirloom apple varieties, far from the cloyingly sweet mass-market hard ciders you’ll find at supermarkets. The tasting room, constructed from a salvaged early nineteenth–century timber frame, serves cheese plates along with flights of the cider. An outdoor oven is being built to add to the food offerings this summer.

Even if you’re not staying at the Harraseeket Inn, its restaurant, Broad Arrow Tavern, makes for an excellent dinner or nightcap option, serving classic yet elevated pub dishes.

Sunday
Coastal explorations

Finish your weekend by getting out on the water. Seacoast Tours of Freeport offers several boat excursions, including tours of oyster farms, lobstering demonstrations, and visits to Eagle Island, the former summer home of Arctic explorer Robert Peary.

Before heading home, make a final stop at Harraseeket Lunch and Lobster Company for a lobster roll. You can sit at one of the picnic tables, watch boats bringing in their fresh catch, and toast to a weekend well spent.

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