Photographs + stories by Maine magazine staff:
Katy Kelleher, Managing editor Maine magazine

Katy Kelleher, Managing Editor

Some people dread December, but not me. Every year as Christmas approaches, I get a giddy, childlike enthusiasm for all things holiday themed. Ugly sweaters? Bring them on. Eggnog? I’ll have two, thanks. So last winter, I was thrilled to learn that I would be heading to Kennebunkport for their annual two-week town-wide celebration. Prelude, as it’s called, comprises a string of events, featuring everything from caroling to church services to glittery galas, and takes place at locations throughout the Kennebunks. With a long list of people to buy presents for, and a car filled with snow gear, I headed south from Portland, ready to experience all the holiday cheer the coastal community has to offer.

Friday

4:00 p.m. @ The Grand Hotel

A light sprinkling of snow is just beginning to fall as I check into my room. My mom will be arriving from Massachusetts shortly, and I settle into the cushy chairs to sip hot chocolate and wait for her. We’re staying in one of the Grand’s artist suites, and this one features paintings by Allen Bunker. His hazy, abstracted landscapes complement the muted, soft colors of winter.

5:00 p.m. @ The Gallery at the Grand

I meet my mom in the parking lot to help her with her bags. She’s red-checked from the cold and excited about the weekend; like my hair and eyes, my love for the holidays was inherited directly from this woman. We drop off her bags and stop in downstairs to visit my friend Leanne, who is working the desk at the gallery. We wander though the intimate gallery, staring longingly at paintings by Jill Hoy, Ann Sklar, William Crosby, and other Art Collector Maine artists. “I wish my walls looked like this!” my mom says.

5:30 p.m. @ David’s KPT

We heard that the best way to catch the Friday night fireworks is grabbing a seat on David’s waterfront deck. We bundle up and enjoy a few cocktails alongside a crowd of revelers. The sky bursts with color, and the water below glistens with the reflection of all those red, green, yellow, and blue explosions. What a way to start the weekend!

7:00 p.m. @ 50 Local

fter years of being taken care of, it’s nice to be able to treat my mom. We sip glasses of spicy, fruity malbec and dig into heaping bowls of pasta, made fresh with local ingredients.

9:00 p.m. @ The Hive

Before we head back to the hotel, we stop at this cool little venue, which hosts art exhibits, live music, classes, and community gatherings. I’m too tired to stay long, but we sip our nightcaps while enjoying a few minutes of acoustic guitar.

Saturday

8:30 a.m. @ All Day Breakfast

The atmosphere inside All Day Breakfast is cozy and comfortable. People at different tables lean across to chat with each other, and a group of older men joke gruffly with their smiling waitress. It’s always a pleasure to observe a tight-knit community like Kennebunk—this is especially true in the off-season, when residents are left to relax, reconnect, and enjoy the quiet nature of a Maine winter.

9:30 a.m. @ Goose Rocks Beach

The thermometer on the dashboard reads 7 degrees, which naturally means it’s time to go to the beach. While many of Maine’s shores are rocky and rough, this one is sandy and smooth—the perfect surface for walking off breakfast.

10:30 a.m. @ St. Anthony’s Monastery and Franciscan Guesthouse

We continue our winter walk at this beautiful old 66-acre property. In the summer, gardens bloom with vivid colors, but it’s equally lovely in winter. We wander from woods to waterfront, admiring the many statues along the way. As we explore, my mom fills me in on the latest news from my three siblings. We stop to light a votive candle in the chapel before leaving.

11:30 a.m. in the Lower Village

A massive nor’easter is forecast for tomorrow, so we decide to do our Christmas shopping while we still can. In honor of Prelude, many stores are offering special sales, hot chocolate, and cookies to customers. We spend a long time picking out a wedding gift for my older brother at Abacus (we settle on a hand-carved wooden clock with a ceramic tile panel), before heading over to Compliments Gallery. I buy a gorgeous, soft plaid scarf at Best of Everything. I intended to give it as a gift, but end up wrapping it around my neck to ward off the icy air.

1:00 p.m. @ Pier 77 and The Ramp

My friend and coworker, Cyndi Smith, and her daughter, Chloe, are meeting us for a mother-daughter lunch at the Ramp. On the drive over, I can’t help but notice that Cape Porpoise in the winter is absolutely stunning. I force my mom to pull over so I can snap a picture of a Christmas tree made of lobster traps. By the time we get to the Ramp, I’m starving. I order a hearty bowl of seafood chowder, which comes with huge bites of haddock and a rich, creamy broth. We discuss our holiday plans while marveling at the eclectic decor inside this popular eatery. Everything is casual, homey, and thoroughly Maine.

2:30 p.m. @ Maine Art Gallery

Across the street from the hotel is a metal garden of floral-like sculptures. These pieces are by artist Lyman Whitaker. It’s a gray day, but the wind plays with the organic-inspired shapes, creating a rather cheerful scene. Inside, the two-story building is an art lover’s heaven, complete with abstract oil paintings, dreamy seascapes, and striking sculptures.

5:00 p.m. @ Bandaloop

With a storm looming, my mom decides to beat the weather and drive home. I call a few friends, and we meet at Bandaloop for appetizers and cocktails. I order their signature white peach margarita and the crunchy, fresh kale salad—both are pitch-perfect.

7:30 p.m. @ Nonantum Resort

The annual Fire and Ice event is taking place tonight, transforming the beautiful oceanfront hotel into a winter wonderland. Outside, ice sculptures glow red with lights, and an ice bar offers guest a chance to sample subzero-temperature beverages. I stand by a bonfire to keep warm, watching the sparks shoot skyward as I chow down on a hot slice of thin crust pizza, baked at an outdoor oven just steps away.

Sunday

10:00 a.m. @ Mornings in Paris

After my eventful evening, I decide to sleep in. I wake to a town covered by two feet of snow. I make my way through the streets slowly. Everything is quiet—sound is muffled by snow and few cars have ventured out in this weather—but Mornings in Paris is open. Shiny gold baubles hang from the ceiling, and I watch the chandeliers twinkle as I sip my coffee.

10:30 a.m. in the Lower Village

Church bells ring out and I hear carolers singing faintly as I wander through town. A few shops have opened, including pet boutique Scalawags, where I purchase gifts for my two dogs. At Daytrip Society I find presents for all my siblings, including my notoriously difficult to buy for younger brother (a book on camping is the perfect gift for that outdoorsman). I’m enchanted by the jewelry in both Benoits and Minka, two lovely shops that specialize in unique local goods (Minka) and chic clothes (Benoits).

12:00 p.m. @ Hurricane Restaurant

Trudging through the snow is hard work, so by the time I find an open restaurant, I’ve worked up quite an appetite. Hurricane is serving brunch, and I order a bloody mary and a plate of piping hot eggs. My drink arrives, and I’m charmed by the tasty shrimp garnish. It’s that attention to detail that makes Hurricane stand out—not to mention its classy dining room, complete with a beautiful riverfront view. I linger at my table, watching the snow fall on frozen water and watching as other diners come and go.

1:30 p.m. on Log Cabin Road

My drive home is tricky, thanks to the difficult weather. But the slow going gives me time to reflect on the town I’ve just left. Maine, I’ve found, is filled with communities like the Kennebunks—places where locals are proud, yet welcoming, where the overall vibe is worldly, yet still thoroughly New England. As I pass the Seashore Trolley Museum, I’m reminded of another trait that seems so typically Maine: a desire to preserve and protect the past, to celebrate the very vehicles that brought us here. I fight the impulse to pull over and explore; the museum is closed for the season, but I promise myself, I’ll be back as soon as the snow thaws.