Planning a bed and breakfast getaway is all about finding the right time to capture the local charm, and Maryland is the ideal destination for every season. Whether you’re looking for crisp autumn foliage, vibrant spring festivals, cozy winter retreats, or sunny summer adventures, there’s a time of year that’s perfect for you. Tacaro Estate, a charming Annapolis, MD, B&B, combines classic Maryland warmth with local seasonal highlights for a stay that’s unforgettable year-round. Here’s our guide to the best times to visit a bed and breakfast in Maryland, and the events and experiences each season brings.

Spring: Blooms and Festivals (March to May)

Maryland comes alive in the spring with blossoming gardens, mild weather, and a sense of renewal. Spring is the perfect time to stay at a bed and breakfast in Maryland if you’re seeking a peaceful retreat surrounded by natural beauty. Tacaro Estate and its surrounding areas offer plenty of outdoor activities, gardens, and local events to experience.

Seasonal Highlights:

• Cherry Blossom Season: A little over an hour from Annapolis, Washington, D.C. hosts its annual Cherry Blossom Festival in March and April, showcasing over 3,000 cherry trees in bloom along the Tidal Basin. The festival features parades, food vendors, and cultural performances, making it a fun day trip. 
• Maryland Day: This weekend-long event in March celebrates Maryland’s founding and offers free access to museums, historical sites, and parks across Annapolis and surrounding areas. It’s a great way to explore Maryland’s heritage and culture.
• Preakness Stakes: In May, Pimlico Race Course in Baltimore hosts the famous Preakness Stakes, the second jewel in the Triple Crown of thoroughbred racing. Plan a visit to experience this iconic Maryland event, and enjoy the high-energy atmosphere, food, and local traditions.

Spring is also the ideal time to explore Maryland’s gardens. The grounds at Tacaro Estate showcase vibrant spring blooms, offering a picturesque setting for morning walks and afternoons in the sun.

Summer: Seaside Escapes and Sun-Soaked Fun (June to August)

Summer is one of the most popular times to visit a Maryland bed and breakfast, and it’s easy to see why. The warmer months bring opportunities for sailing, beach days, and vibrant festivals along Maryland’s coastline. Annapolis is known as the “Sailing Capital of the U.S.” and offers countless ways to enjoy the water and nearby sandy shores.

Seasonal Highlights:

• Maryland Seafood Festival: This annual September festival celebrates Maryland’s seafood heritage, featuring crabs, oysters, and other local favorites. Held at Sandy Point State Park, approximately 20-minutes from our grounds,  it’s the perfect place to sample fresh seafood, enjoy live music, and try cooking demos.
• Fourth of July Festivities: Annapolis is famous for its Fourth of July celebrations, with a boat parade, waterfront fireworks, and a patriotic parade through historic downtown. Visitors can watch the dazzling display over the water for a truly memorable experience. Our grounds are within driving distance of Washington D.C., making it the perfect place to stay while venturing in to see fireworks on the lawn of the Capitol. At Tacaro we also host live music with music star Ryan Forrester and a BBQ for our guests! 
• Sailing Excursions: Summer is the best time to take advantage of Annapolis’s sailing opportunities. Book a sunset cruise on the Chesapeake Bay, try paddleboarding, or tour the harbor to get a true sense of Maryland’s maritime heritage. 

For those who prefer a slower pace, Tacaro Estate offers the perfect setting to unwind with a refreshing summer breeze. Enjoy breakfast on the veranda, explore the estate’s manicured gardens, or relax in the fully air conditioned  reading room with a view of the lush surroundings.

Fall: Foliage and Harvest Festivals (September to November)

As temperatures begin to cool, Maryland’s landscapes transform into a canvas of red, orange, and yellow hues. Fall is one of the best times to visit a bed and breakfast in Maryland, with scenic drives, harvest festivals, and cozy evenings around the fireplace. Tacaro Estate provides the perfect backdrop for a relaxing autumn getaway, with a view of the changing leaves and seasonal treats.

Seasonal Highlights:

• Maryland Renaissance Festival: From late August through October, this festival in Crownsville brings history to life with period costumes, jousting, artisan crafts, and theatrical performances. The Renaissance Festival is a family-friendly event that draws crowds from across the state.
• Oktoberfest: Maryland’s German heritage is celebrated with Oktoberfest events throughout the fall, featuring craft beer, authentic German food, and live music. Check out the Oktoberfest in Frederick or the Das Best Oktoberfest in Baltimore for a taste of Bavarian culture.
• Wine Harvest Festivals: Maryland’s vineyards celebrate the harvest season with tastings, vineyard tours, and fall festivals. The Maryland Wine Festival in Westminster is a local favorite, where you can sample wines from over 25 local wineries while enjoying live music and artisan markets. At Tacaro Estate, we’re proud to serve a curated selection of seasonal wines from local Maryland vineyards, allowing you to continue exploring Maryland’s rich wine offerings right here. If you find a new favorite wine at the festival, there’s a good chance it will be available at the estate, offering you a taste of Maryland’s vineyards all season long.

Tacaro Estate captures the spirit of autumn with seasonal décor, warm drinks by the fireplace, and fall treats that bring out the flavors of the season. It’s an ideal time to snuggle up and enjoy the crisp air, scenic drives, and Maryland’s festive fall events.

Winter: Cozy Retreats and Holiday Cheer (December to February)

Winter at a bed and breakfast in Maryland is the definition of cozy. While the weather may be chilly, the atmosphere at Tacaro Estate is warm and welcoming. This is the season for holiday lights, winter festivals, and cozy nights by the fire. Whether you’re looking for a romantic escape or a holiday-themed getaway, winter is a charming time to visit.

Seasonal Highlights:

• Midnight Madness in Annapolis: During December, Annapolis celebrates with Midnight Madness, a series of festive shopping events where shops stay open late and the city is lit up with holiday lights. Enjoy carolers, hot cocoa, and a festive atmosphere while shopping for unique holiday gifts.
• Holiday Candlelight Stroll: Tour historic Annapolis by candlelight on select dates in December. These guided tours offer insight into the city’s past, along with stories and décor that evoke the spirit of an old-fashioned Christmas.
• Chesapeake Bay Christmas Light Boat Parades: During the holiday season, Chesapeake Bay comes alive with dazzling Christmas light boat parades, featuring beautifully decorated boats lighting up the water. Annapolis and other nearby areas host these festive events, where locals and visitors gather to watch the colorful displays, bringing holiday cheer to the waterfront.
• Ice Festivals: The Fire & Ice Festival in Frederick in January and Easton’s Ice Festival in February feature ice sculptures, live demonstrations, and winter-themed events. These festivals bring the community together for family-friendly fun during the colder months.

Tacaro Estate offers a warm and welcoming space to return to after a day of winter activities. Guests can enjoy fireside wine tastings, gourmet breakfasts, and an intimate, relaxed setting that captures the best of Maryland’s winter charm.

Your Year-Round Maryland B&B Escape

Each season offers a unique reason to visit Maryland, and Tacaro Estate provides a bed and breakfast experience that captures the charm of each one. From blooming gardens and sailing adventures to fall foliage and winter holiday magic, there’s something for every traveler at every time of year.

So whether you’re planning a spring escape, a summer retreat, an autumn adventure, or a cozy winter getaway, Tacaro Estate’s Annapolis B&B is the perfect place to experience Maryland’s seasonal highlights. Visit Tacaro Estate and book your stay to discover the local events, scenic beauty, and year-round charm Maryland has to offer.