Fall is one of the most beautiful times to visit the Chesapeake Bay region, and October is when the area truly shines. If you’re planning a getaway to Tacaro Estate, you’ll find that the charm of the season extends far beyond the estate gates. Whether you’re here for a relaxing weekend, a fall wedding, or a quick escape from the city, here are some of the best things to do in and around Washington DC, Tracy’s Landing, North Beach, Chesapeake Beach, and Annapolis in October.
1. Stroll the North Beach Boardwalk
Just a short drive from Tacaro, the North Beach boardwalk is the perfect place for a peaceful morning walk or a romantic sunset stroll. In October, the air is crisp, and the beach is quieter, making it ideal for enjoying the views without the summer crowds. Bring a coffee from a nearby café and take in the fall colors along the water.
2. Dinner at Baia Coastal Italian
Fall is for cozy, comforting meals, and Baia Coastal Italian in North Beach delivers. Their waterfront patio is still open on mild evenings, and the indoor space is warm and inviting. Seasonal ingredients shine on their menu, with dishes like butternut squash ravioli and hearty pastas that feel just right for autumn. It’s a favorite date night spot for Tacaro guests.
3. Explore Historic Annapolis
October is a fantastic time to explore Annapolis. The brick-lined streets are framed by golden trees, and the waterfront remains lively without the summer heat. You can visit the U.S. Naval Academy, browse boutiques on Maryland Avenue, or join a historic ghost tour, a local favorite in the weeks leading up to Halloween.
4. Local Fall Festivals & Markets
Many local farms and communities host fall-themed events throughout the month. Look for pumpkin patches, apple picking, hayrides, and craft fairs in nearby areas like Davidsonville and Deale. Tacaro staff are always happy to recommend their favorite hidden gems for seasonal fun.
5. Wine Tasting at Thanksgiving Farm Winery
Located just minutes from Tacaro, Thanksgiving Farm Winery is a serene spot to sip local wines surrounded by colorful fall foliage. Their tasting room is cozy and quiet in October, and the property’s views are worth lingering over. Pack a picnic or grab some cheese and crackers from their shop for a relaxed afternoon.
6. Cozy Up by the Fire at Tacaro
Of course, one of the best parts of October at Tacaro is doing… absolutely nothing. After a day exploring the region, there’s nothing better than returning to your suite, lighting the fireplace, and sinking into a plush chair with a good book or a glass of wine. Nearly every room at Tacaro includes a fireplace, and fall was made for evenings like these.
7. Book a Fall Photoshoot on the Grounds
If you’re visiting for a romantic getaway or celebrating a special moment, October is an amazing time to capture the beauty of the estate. The trees are vibrant, the gardens are peaceful, and the lighting is soft and golden. We often recommend booking a local photographer to document your time here. Tacaro is perfect for engagement photos, anniversary shoots, or just a personal keepsake of your stay. Check out some of the photos Tacaro guests have taken on our social media!
Plan Your October Escape
Whether you’re here for one night or a long weekend, October offers some of the best experiences near Tacaro Estate. From crisp walks on the boardwalk to local wine tastings and fireside evenings, fall in the Chesapeake Bay area is something special.
Looking to book a last-minute autumn getaway? A few rooms may still be available, visit our booking page to reserve your stay!