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Lucy’s Holly Jolly Holiday in Portland, Maine

By Peggy Newland - Correspondent | Dec 10, 2025

Getting a cookie after shopping in Portland. Courtesy photo/BRIAN GOETZ

Lucy doesn’t like the elevator, with the bells, and sliding door, but the friendly concierge crouches down, holding the first of what will become a “cookie” weekend for Lucy. Since we are here to celebrate the festivities in Portland, Maine, and we are staying at Cambria Portland Downtown-Old Port, this is the start of pre-holiday happiness.

Lucy soon loves the “cookie elevator” and makes herself comfortable in the merry lobby, festooned by holiday lights, an evergreen tree, and outdoor igloos for dog-friendly dining later that evening. The room is comfortable, with nautically inspired décor, feather pillows, a “couch with a view” for Lucy, and floor to ceiling windows overlooking the Portland Harbor. We are perfectly situated near the Old Port, the walking trails of the East End, and the gorgeous Eastern Promenade, with its narrow-gauge railroad, its polar plunge beaches, Portland Observatory, and funky decorated neighborhoods of Munjoy Hill.

Lucy and I head to the cobblestones of the Old Port for a galivant and to check out the lobster trap tree, the holiday light installations around town, and the bedazzled mansions of the Western Promenade. Soon, we find ourselves shopping on the dog-friendly Merry Madness Crawl. Collecting stickers at each shop, we are entered for grand prizes when we buy holiday gifts. I hope for a new bicycle and Lucy is wishing for that lobster-themed sweater.

After “shopping and snacking,” we grab more “elevator cookies” before taking in the Parade of Lights on the Casco Bay. We find a bench on the Eastern Promenade with other revelers and watch blinking, lit up tugboats, lobster boats, ferry boats trumpeting in the season of light. Classic carols start up and soon we are all singing tunes like “Happy Holidays” and “Rudolf the Red Nosed Reindeer.” Lucy wags her tail with delight.

That night, on the Alto Terrace, we dine in an igloo, swanked out with a couch, tunes, flannel blankets, pillows, and heating lamps. Party lights drape over the interior and it’s a celebration of cuisine in the best way, as Lucy gets to greet the staff every time they unzip our igloo, bringing in delicacies like lobster stuffed mushrooms in lemon and tarragon aioli, farmstand salad, and steak frites. Lucy enjoys some snips of tenderloin.

Holly Jolly Lucy. Courtesy photo/BRIAN GOETZ

After dinner, we stroll along the Promenade. Lucy and I watch the lit up Narrow Gauge holiday train curve around the coves and beaches. The distant view of harbor lights twinkling on piers and walkways below us give off holiday vibes, even with the winds coming off Casco Bay. With a scarf bundled around my neck, and Lucy pulling us back down the hill, we are welcomed back to the Cambria–cookies at the front desk, hot toddy in my hand, a firepit lit. A celebration of early winter before the crush of holidays.

Cambria Portland Downtown-Old Port. www.cambriaoldport.com. 25 Hancock Street, Portland, Maine. Cambria can be reached at 207-800-3421. Ask for the Paws are Welcome package and get treats in the room, at the front desk, and a personalized water bowl for your happy hound.