It’s Thanksgiving Day, and you are ready to tackle the day and create lifelong memories with your closest friends and family. Start your day with some well-deserved me time and a strong cup of organic coffee from Petticoat Row Bakery, a downtown bake shop that is open year-round and offers freshly homemade delectable sweets and artisan breads. Steps away from Hotel Pippa, it also offers scrumptious breakfast sandwiches on freshly baked biscuits.

Grab a pair of sneakers and head to the Thanksgiving 5k race, organized every year by the Nantucket Triathlon Club. It never hurts to get a quick run in before sitting down for Thanksgiving dinner with the family. The race typically meanders around Brand Point and up to the Cliff, offering stunning views along the way.

Next, you can choose to join an annual Nantucket tradition – the Cold Turkey Plunge at Children’s Beach. The most adventurous islanders plunge into 20-, 30-, and sometimes 40-degree water without a wetsuit. The event benefits a local charity and is always a lot of fun!

After a warm shower, head over to the Nantucket Fish & Meat Market to get a feel for the town’s energy as families stock up for their Thanksgiving Feast. We would recommend also visiting Bartlett Farm for produce and Annye’s for the most divine prepared sides and dishes.

If you’d like to contribute to the menu, you can try your hand at scalloping and bring some Nantucket scallops back home to serve as delicious locally-sourced appetizers. Sauteed Nantucket Bay scallops are a true delicacy and can be easily and quickly prepared while the rest of the kitchen handles the turkey, stuffing and more.

If the weather allows, take a bike ride out to Cisco Brewers and indulge in their tasty spiked cider to warm up. You can also stock up on their seasonal brews, Nantucket Vineyard wines or vodka, gin or whiskey from Triple Eight Distillery. You can also join the public tour before heading back, a short but very informative tour that covers the operating procedures and methods of a functional winery, brewery and distillery.

Countless restaurants on island offer Thanksgiving dinner but reservations are recommended. Menus blend local produce, freshly fished seafood and high-quality meat with traditional Thanksgiving dishes, promising a memorable dinner in a cozy environment. The front desk team at Hotel Pippa can assist with reservations in anticipation of the Thanksgiving weekend.

The day after Thanksgiving also marks the start of the holiday season, a magical time on the island. Nantucket Noël kicks off with the much-anticipated Christmas Tree Lighting & Caroling ceremony. Locals and visitors alike gather on Main Street and anxiously wait for the Town Crier to start the traditional countdown.

All of a sudden, 100 Christmas trees magically illuminate the central cobblestone thoroughfare, bathing islanders in a blaze of colored lights. Traditional holiday carols resonate through the streets, led by talented local a cappella groups. The event kicks off a busy holiday season full of festivities and activities, giving visitors and locals alike reasons to come back over and over again before the year wraps up.