Sometimes, the best way to reconnect is to leave the city behind for a few days. If you’re searching for weekend getaways from Baltimore, Maryland’s Eastern Shore offers a refreshing change of pace just 90 minutes away.
Chestertown combines waterfront scenery, historic charm, exceptional dining, and opportunities to slow down together. Spend your days exploring the Chester River, browsing local galleries, and discovering one of Maryland’s most picturesque small towns. Then return to Brampton 1860, where peaceful gardens, luxurious accommodations, and thoughtful hospitality create the perfect setting for a romantic escape.
Why Chestertown Is One of the Best Weekend Getaways from Baltimore
Looking for a romantic destination that’s close enough for a spontaneous trip but far enough to feel like a true escape?
Chestertown delivers exactly that.
Located on Maryland’s Eastern Shore, this historic waterfront town offers a blend of outdoor recreation, locally owned restaurants and shops, cultural attractions, and small-town charm. Unlike busier destinations, Chestertown invites you to slow down and enjoy each moment.
How Far Is it from Baltimore to Chestertown, MD?
Chestertown is approximately 75 miles from Baltimore. The drive takes about 90 minutes, making it ideal for a two- or three-night getaway.
We recommend crossing the Chesapeake Bay Bridge and following scenic roads through Maryland’s Eastern Shore. Another route travels north through Elkton before heading south on MD-213. Both options offer beautiful countryside views and a relaxing start to your getaway.
Are you ready for a relaxing escape that’s close to home but feels worlds away? Check availability and start planning your Eastern Shore getaway.
1. Reconnect in Nature Along the Chesapeake Bay
One of the biggest reasons guests come to the Eastern Shore is the peaceful respite of unwinding outdoors.
Waterfront landscapes, quiet nature preserves, and abundant wildlife create an entirely different pace than city life.
Popular outdoor experiences near Chestertown include:
- Sunset cruises on the Chester River
- Kayaking and paddleboarding
- Birdwatching at Eastern Neck National Wildlife Refuge
- Hiking at Adkins Arboretum
- Exploring Millington Wildlife Management Area
- Scenic drives through Kent County’s countryside
Guests often tell us that some of their favorite moments happen right here at Brampton 1860. Stroll our gardens, relax beneath mature trees, or settle into an Adirondack chair with a book and a glass of wine.
2. Discover Outstanding Dining on Maryland’s Eastern Shore
A great getaway deserves great food.
If you’re craving classic Maryland seafood or farm-to-table eats, Chestertown restaurants will satisfy any palate. Enjoy some of the freshest seafood you will ever taste, dine beside the water, or have a date night in with a selection from our dining packages.
Chestertown is especially known for blue crab, a Mid-Atlantic staple, so make sure to try some while you’re in town. From intimate cafes and bistros to fine dining establishments, you’ll find a little bit of everything in Chestertown.
Here at Brampton 1860, your culinary experience is also an important part of your day.
Each morning starts with a gourmet breakfast prepared fresh by our culinary team. You’ll enjoy fresh, flaky pastries, pancakes, bacon, eggs your way, and more. We’ll gladly deliver breakfast right to your doorstep if you request it!
In the afternoons, come back to the inn for our Tea Time and social hour. All of our savories and sweets are freshly prepared each day using local, seasonal ingredients.
3. Explore Historic Sites, Museums, and Local Art
Few small towns in Maryland offer as much history and culture as Chestertown.
Founded in 1706, Chestertown is one of the state’s most historic communities. Its beautifully preserved downtown features brick sidewalks, colonial architecture, and numerous buildings listed on the National Register of Historic Places.
Chestertown’s Historic District
The town has nearly two dozen spots listed on the National Register of Historic Places. Take a self-guided walking tour and see them all during your visit.
Washington College
Founded in 1782 with support from George Washington, Washington College remains a centerpiece of the community and hosts cultural events throughout the year.
Harriet Tubman Underground Railroad Byway
Learn about one of the most important chapters in American history, Harriet Tubman Underground Railroad. Take some time to explore the sites connected to Harriet Tubman’s extraordinary legacy.
Local Art Galleries
Art lovers will discover galleries in Chestertown with rotating exhibits throughout the year. Take your time browsing local masterpieces at RiverArts, MassiniArt or the Create Galleries. You’ll find paintings, textiles, jewelry, pottery and sculptures.
Make Brampton 1860 Your Home Base on the Eastern Shore
A memorable weekend getaway from Baltimore starts with the right place to stay.
Set on 35 acres just outside downtown Chestertown, Brampton 1860 offers a peaceful retreat that feels worlds away from everyday life while keeping you close to the area’s best attractions.
Guests can choose from elegant guest rooms and secluded cottages designed for comfort, privacy, and relaxation.
Looking for a Longer Escape?
Our Robin’s Nest Cottage is especially popular for extended stays. With spacious accommodations, a private setting, and easy access to the best of Maryland’s Eastern Shore, it’s an excellent choice for couples looking to fully embrace a slower pace.
What season is best for your getaway? Spring bursts with new life as our gardens begin to bloom. Summer vacations by the water are hard to beat. Fall brings a peaceful calm and a bountiful harvest. While winter offers cozy comfort and sweet snuggles by the fire.
For even more relaxation, enhance your stay with:
- In-room massage services
- Romantic add-ons
- Fresh flowers and champagne
- Seasonal packages and special offers
- Gourmet breakfasts each morning
Check Availability and Start Planning
If you’re searching for one of the best weekend getaways from Baltimore, Chestertown offers the perfect combination of romance, history, dining, and outdoor adventure.
Check availability at Brampton 1860 and discover why so many couples return to Maryland’s Eastern Shore year after year.
Photo Credit: © IOFOTO via canva.com, © Cesar Okada from Getty Images Signature via canva.com, © Otovect-Media from pixabay via canva.com, © Better Living Magazine
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