Friday Evening
Oceanside lodging and can’t-miss sights

It’s worth starting your trip at the iconic, and practically mandatory, Fort Williams Park in Cape Elizabeth. Built in 1899 as a defensive U.S. Army fort, the 90-acre park is now home to several popular recreational sites, including what might be America’s most photographed lighthouse, the Portland Head Light, and the Children’s Garden. Motor coach tours give an in-depth look at Maine’s extensive military history. Dressed in wreaths and bows, the lighthouse and its environs feel quietly festive in the holiday months.

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Not far from Fort Williams is a lovely cafe, market, and bakery, C Salt Gourmet Market, where you can stock up on picnic provisions on your way to the park. The sandwich menu is expansive and well executed, and there are sweet treats and snack options for everyone in your cadre (and plenty of wine offerings, although that you’ll have to leave those behind when entering the park).

After allowing yourself to get lost for a while at these grounds by the ocean, shoot straight down Shore Road to the Inn by the Sea. One of Maine’s finest hotel offerings, the Inn by the Sea is an all-season resort that caters to anyone looking for luxury and views. As a bonus, the hotel is very pet-friendly and welcomes any pups you might want to bring as fellow guests. With roaring fires and a well-stocked bar, the lobby is a lovely place to hunker down in cooler temperatures. To avoid said cold, stay at the inn for dinner at its restaurant, Sea Glass. With a menu encompassing dishes like lobster tacos, local duck, and pork osso bucco, why venture out?

Saturday Morning
Scenic walks and Knightville exploring

Nearly right outside the door of the hotel is Great Pond Trail, a walking path surrounding Cape Elizabeth’s 40-acre freshwater Great Pond. It’s perfect for a brisk pre-breakfast stroll or, once the pond has frozen, ice-skating. In the summer, boat racks are awarded via lottery, and there’s beach access to launch your vessel onto the pond. Once you’ve sufficiently worked up an appetite, drop by The Cookie Jar Pastry Shop for arguably (and people certainly do argue about it) the best doughnuts in Maine.

For those seeking Atlantic vistas to pair with their morning coffee, a walk along Higgins Beach in Scarborough is highly recommended. Parking can be tricky at this sandy beach, especially during the summer, but rest assured it’s worth looping around the block a couple times.

A short drive lands you in South Portland’s Knightville neighborhood, an area perfect for shopping. Stop in at Ocean and D Goods for a handpicked selection of gifts. The owner, Emma Lockwood, focuses on small, largely female-led businesses, and the offerings include jewelry, leather goods, and interior design accoutrements. Should you find shopping draining, head up the street to Foulmouthed Brewing for a quick nip and a recharge. Before leaving the area, pop into Nonesuch Books and peruse the Maine authors section, with tomes from Stephen King, Tess Gerritsen, Elizabeth Strout, and Lily King among others.

Saturday Afternoon
World-class art and spa bliss

Back at Fort Williams Park is the Rachel Walls Fine Art gallery, a cultural gem currently displaying the work of artists Cabot Lyford, Dahlov Ipcar, and Robert Andrew Parker. Curator Walls has an exhaustive background, having organized exhibitions and tours at places like the Los Angeles County Museum of Art, the Georgia O’Keeffe Museum, and the San Francisco Museum of Modern Art, among others. That each artist in the gallery has a Maine connection only makes the space that much more worthy of a tour and, if you’re lucky, a chat with Walls herself.

On your way back to the Inn by the Sea to take advantage of its state-of-the-art spa, grab a late lunch at The Good Table. This family-owned community favorite serves everything you actually want to eat, including fried clams, butterscotch pudding, and a delicious seasonal Thanksgiving sandwich. Stuffed, you really have no option but to go lie on a massage table for an hour. The expert staff at the spa at the Inn by the Sea is accommodating and willing to tailor your treatment to anything that needs focusing on. Book the facial and massage combo for optimal indulgence. Provided you don’t need to take a nap at this point, take a quick trip to The Old Farm Christmas Place; whether you’re looking for a tree come Christmas or just to take in the smell of balsam, it’s a beautiful spot to gaze at those impressive Maine firs.

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Saturday Evening
Up-and-coming dining

The Dunstan neighborhood in Scarborough is building up quickly, and at the front of that curve were Brian and Jen Brenerman with their restaurant Dunstan Tap and Table. It’s a great place for a big group, or to grab dinner with a friend (or date) at the bar. They keep a fire pit going outside, which pairs quite well with a negroni and a sweater. The poutine gives Montreal a run for its money, and the burger is deadly.

Sunday Morning
Baked goods worth waiting for

You don’t want to miss the pastries at Scratch Baking Company in South Portland. Few places actually merit queueing up, but the bagels, cinnamon buns, and cookies here appropriately draw visitors from all over the area and are worth the line. Your family will thank you if you pack some bread to take home as a souvenir. (Grab some brie at The Cheese Iron if you really want to win them over.) On your way to Scratch, take a moment to pull over and peek a look at the historic Spurwink Congregational Church in Cape Elizabeth, the town’s oldest building. This architectural beauty was built in 1802 and still serves as an important meeting place for members of the community.

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Stocked up with baked goods, take a quick drive to Pine Point Beach in Scarborough. This long beach, which extends from the Pine Point jetty to Old Orchard Beach, is beloved by locals and tourists alike, and is a great place to bring a cruiser and head out for a bike ride. In the summer, nostalgic food shacks make for convenient places to grab lunch. When it’s chillier, it’s a rare opportunity to get some of the coast to yourself.

Finally, on your way out of town, pick up today’s catch at Pine Tree Seafood and Produce. Its proximity to the Atlantic means you can still taste the brine on the fresh scallops, oysters, and lobsters. Paired with that morning’s fresh bread, your loved ones will almost forgive you for leaving them behind.

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