Local Favorites and Queenstown Harbor Winter Experiences
The holiday season is here, and there’s no better time to explore the Eastern Shore’s festive charm. Meanwhile, from cozy winter activities to unique shopping experiences, Queen Anne’s County, Easton, Annapolis, and surrounding areas offer something for everyone this December. Whether you’re planning a family outing, a girls’ night, or a full winter getaway, ultimately, make the most of the season with these local favorites and Queenstown Harbor experiences.
Festive Fun at Queenstown Harbor
Ladies Night – December 16 | 4:00 – 7:00 PM
Grab your friends for a night out at Queenstown Harbor! Our heated Toptracer range sets the scene for an evening of laughs, holiday drinks, and friendly competition. It’s the perfect way to celebrate the season with style and warmth. Our toptracer bays are fully reserved, but all are welcome to sip & shop at the Smith & Quinn Trunk Show or make some friends and hit a few balls in the reserved bays. Learn More Here
Swing with Santa – December 22 | 3:00 – 6:00 PM
Bring the kids and get into the holiday spirit with a visit from Santa at Queenstown Harbor! Snap a memorable photo and enjoy our heated Toptracer driving range. Perfect for families or anyone looking to combine holiday cheer with some winter golf fun. Complimentary Hot Chocolate Bar for the kids with a fun festie upgrade for the parents available. Learn More Here
Tavern Specials
Winter at Queenstown Harbor isn’t just about activities, it’s about savoring the season. Our tavern features special seasonal menus and drinks weekly, making it the perfect spot to unwind after a day on the course or exploring the Shore.
Local Holiday Favorites
Quiet Waters Outdoor Ice Rink – Annapolis | All Winter
Looking for a classic family activity? Quiet Waters Park in Annapolis offers outdoor ice skating throughout the winter. Glide under the crisp winter sky and enjoy a day full of laughter, hot cocoa, and holiday spirit.
Learn more here
Lights on the Bay – Sandy Point State Park | All December
Experience a magical drive-through holiday display at Sandy Point State Park. Lights on the Bay features dazzling decorations and festive installations, all while supporting the SPCA. Perfect for families or couples seeking a cozy holiday evening.
Learn more here
Midnight Madness – Downtown Annapolis | Thursdays in December
Shop, dine, and explore Downtown Annapolis during extended hours with Midnight Madness. Every Thursday before Christmas, local shops, restaurants, and bars stay open late for holiday shoppers, making it a fun night out for friends, couples, or solo explorers.
Learn more here
Holiday Shopping in Queenstown and Beyond
The Eastern Shore is home to unique boutiques, artisanal gifts, and charming local shops. Queenstown’s cozy streets are perfect for finding one-of-a-kind holiday presents, while a short drive to Easton and Annapolis offer a mix of historic charm and modern shopping experiences. Combine your shopping trip with Queenstown Harbor’s winter activities for a full-day holiday adventure.
Looking for a Full Visit Holiday Itinerary?
Here’s a curated 4-day Winter Holiday Getaway itinerary for December 19–22, blending Queenstown Harbor experiences, local holiday events, dining, and shopping.
Day 1 – Friday, December 19: Arrival & Cozy Evening
- Afternoon: Arrive at Queenstown Harbor at 4:00pm and settle into your waterfront cottage. Take a leisurely walk along the shoreline or forest trails to enjoy the crisp winter air.
- Evening: Enjoy dinner delivered to your cottage at 6:00pm, featuring seasonal specialties and winter cocktails. Unwind by the firepit with a hot drink while taking in scenic water views. Cozy up for a holiday movie in the living room as a family and play a fun holiday game or exchange white elephant gifts as a lead up to your holiday festivities.
Day 2 – Saturday, December 20: Downtown Annapolis & Holiday Fun
- Morning: Head to Annapolis for a day of winter holiday experiences, but make sure to stop by a Little Lovely Coffee House first for festive seasonal drinks. Skate at Quiet Waters Outdoor Ice Rink and enjoy a romantic spin on the ice.
- Afternoon: Explore Annapolis’ historic district for holiday shopping, local crafts, and lunch at a waterfront restaurant.
- Evening: Experience Lights on the Bay at Sandy Point State Park, followed by a hot cocoa or dessert stop on the way back to your Queenstown Harbor Waterfront Cottage.
Day 3 – Sunday, December 21: A Day in Historic Downtown Easton
- Morning: Start with a cozy brunch at Queenstown Harbor’s Tavern, then head to Easton, just a 30 minute drive from Queenstown Harbor.
- Afternoon: Boutique shopping and a light on the go walking lunch from one of the downtown restaurants.
- Evening: Dinner in Easton at a local favorite, followed by an optional stroll to enjoy holiday lights. Some our staff’s favorite restaurants include Scossca and The Pub.
Day 4 – Monday, December 22: Queenstown Shopping, Swing with Santa & Departure
- Morning: Check out of your waterfront cottage by 11:00 AM. Warm up at Queenstown Harbor’s tavern for an early lunch, then explore the quaint town of Queenstown, the Queenstown Premium Outlets, and maybe treat mom to a spa treatment at SALT Wellness. Still looking for a gift for the golf-lover in your life? Stop by out pro shop and our golf professionals will be more than happy to help you find the perfexct holiday shopping deal.
- Afternoon (3:00–6:00 PM): Swing with Santa at Queenstown Harbor, take festive photos, enjoy treats, and practice on the heated driving range before you head home, in the perfect festive spirit. Looking for a little competition? Compete in our Week 4 Toptracer mini-challenge for a chance to beat out the rest of the families for a daily team winner prize!
Make This Season Unforgettable
From family fun on the ice and magical light displays, to warm evenings at Queenstown Harbor, the Eastern Shore is brimming with holiday cheer. Plan your visit to experience the best winter activities, festive shopping, and cozy seasonal specials, all while soaking in the charm of Maryland’s Eastern Shore.
✅ Extra Tips:
- Dress in layers: Eastern Shore winters are chilly but often bright and sunny.
- Book any winter golf or Toptracer sessions in advance to secure your spot.
- Check event websites for exact hours, especially Lights on the Bay and Annapolis holiday events.
Tip: Don’t forget to check Queenstown Harbor’s calendar for seasonal events, driving range specials, and tavern offerings throughout the winter