Hi friends! It’s me, Tica, your Chief Happiness Officer for the Brad Kappel Team. The holidays around Annapolis and Anne Arundel County are some of the most anticipated and well-loved events of the year, drawing visitors and locals alike to the waterfront for festive traditions, community gatherings, and seasonal adventures. As Maryland’s #1 waterfront real estate team, we believe experiencing the Chesapeake Bay lifestyle means celebrating the season with every member of your household—especially the four-legged ones!
Here’s my updated guide to the best dog-friendly holiday activities across the Chesapeake Bay region! The holidays are my favorite time of year—twinkling lights, festive walks, and so many fun adventures across Annapolis, Anne Arundel County, and the Eastern Shore. And the best part? Your pup can join in on almost all of them!
Here are my top dog‑friendly holiday activities to enjoy around the Chesapeake Bay this season:
🎄 1. Lights on the Bay – Sandy Point State Park
This dazzling drive‑through light display is a must‑see for pups and their humans. The best part? It supports the SPCA of Anne Arundel County, which makes my tail wag even more. Cozy up in the car, turn on some holiday music, and enjoy the sparkling scenes.
🎅 2. Midnight Madness – Downtown Annapolis
Downtown Annapolis transforms into a holiday wonderland with late‑night shopping, seasonal treats, and twinkling lights. Dogs are welcome to stroll down Main Street, inhale delicious scents, and greet holiday shoppers. I love the festive energy (and all the attention!).
⛵ 3. Eastport Yacht Club Lights Parade (Dog-Friendly Viewing Spots)
Bundle up and head to the waterfront to watch boats covered in lights parade across the water, hosted annually by the Eastport Yacht Club. While pups can’t join on board, there are plenty of pet‑friendly parks and patios with perfect views. It’s one of my favorite Chesapeake traditions. Consider watching from the end of Market, Shipwright, and Conduit Streets in downtown Annapolis for a less-crowded view.
🎄 4. Local Holiday Markets & Festivals
Outdoor markets across Annapolis, Severna Park, and the Eastern Shore welcome four‑legged visitors. Browse local crafts and gifts while your pup enjoys fresh winter air, new friends, and plenty of sensory excitement. The Chocolate Binge Festival and Annapolis Holiday Market are the perfect outdoor shopping venues to enjoy with your pet.
☕ 5. Winter Walks + Warm-Up Stops
Explore the cozy streets of Downtown Annapolis, West Annapolis, or Eastport together, then warm up outdoors with a seasonal drink at one of my favorite dog‑friendly coffee shops. (I highly recommend asking your barista for a pup cup!) I also wrote a blog about my favorite pup-friendly coffee shops- you can find that article here.
🌉 6. Day Trips to St. Michaels or Oxford
Across the Bay Bridge, the Eastern Shore is full of holiday charm. St. Michaels and Oxford have beautiful lights, festive storefronts, and welcoming small‑town vibes. Many shops offer dog‑friendly browsing, and the waterfront strolls are magical.
🚶♂️🐾 7. First Day Hikes – January 1
Start the new year with a breath of fresh Bay air! Many Maryland State Parks, including those in Anne Arundel County and across the Eastern Shore, host First Day Hikes on January 1. These guided or self-led walks are dog-friendly and offer stunning winter scenery. Tica loves beginning the year exploring new trails—with plenty of opportunities for sniffs, photos, and adventure.
✨ Why the Chesapeake Bay Is the Perfect Place for Pets During the Holidays
From walkable waterfront towns to dog‑friendly events and outdoor festivities, the Chesapeake Bay offers a lifestyle that keeps both pups and their people happy. It’s the perfect blend of community, charm, and year‑round outdoor fun. But don't take our word for it, come explore and experience it for yourself!
💛 Follow Along for More Holiday Adventures
If you’re looking for the best dog‑friendly places to live, play, and explore, you’re in the right place. For more pup‑approved guides and local tips, visit the Brad Kappel Team blog or follow my adventures at #TicaOnTheBay.
Ready to experience the Chesapeake Bay lifestyle with your pup by your side? Explore more pet-friendly guides, local insights, and waterfront living resources on the Brad Kappel Team blog. Whether you’re searching for a dog-friendly neighborhood, a waterfront retreat, or a home with space for every member of the family, our team is here to help you make your move.
Happy holidays from your favorite waterfront-loving golden retriever! 🐾🎄
