The most romantic things to do in Maryland tend to happen at a slower pace. Here on Maryland’s Eastern Shore, that means a riverfront walk, a wine flight, and a long soak. We’ve welcomed couples to Brampton 1860 for anniversaries, honeymoons, birthdays, and weekends that needed no reason at all.
Over breakfast, guests often tell us which experiences they enjoyed most. We’ve gathered some of their favorites here, along with a three-day itinerary. When you’re ready to pick your dates, check availability for your Chestertown getaway.
What Are the Most Romantic Things to Do in Chestertown, MD?
Chestertown’s most romantic moments are small and unhurried: a riverfront stroll, an afternoon at a gallery, or a candlelit table downtown. Park the car and wander; our historic town is small enough to explore on foot. Our guide to things to do in Chestertown, MD covers museums, shops, and seasonal events.
These are the date ideas we recommend to couples most often:
- Stroll the Chester River waterfront. Start at Wilmer Park and follow the water past homes dating to the 1700s. Late afternoon is especially lovely when the sunlight reflects off the Chester River.
- Browse High Street together. Walk hand in hand as you stop in our galleries, independent bookshops, and boutiques. Stop for coffee when you need a break.
- Spend Saturday morning at the farmers market. The Chestertown Farmers Market fills Fountain Park with local produce, flowers, and baked goods. Pick up something to share on the porch later.
- Taste your way through wine country. Crow Vineyard & Winery pours estate wines a short drive from the inn. Our Eastern Shore wineries guide maps out a longer wine trail for two.
- Take the long way home. Quiet back roads wind past farmland and water across Kent County. Our favorite Chesapeake Bay scenic drives make the journey part of the date.
- Linger over dinner downtown. The Kitchen at the Imperial is one of our favorite tables for two, especially for a classic Maryland crab cake. Our guide to where to eat crab in Chestertown, MD shares a few more spots worth the drive. Ask us for our current picks when you book.
Choose your favorite activities and take your time to relax and enjoy.
How Should You Plan a Three-Day Romantic Weekend in Maryland?
Plan on two nights in a private cottage and one full day to explore Chestertown. Then leave plenty of time unscheduled. The itinerary below follows our Treasured Romance package, available in our Mulberry, Sunrise, Sunset, or Marley’s Cottages. Follow it closely, or borrow the pieces that suit you both.
Day One: Arrive and Settle In
Brampton 1860 is about an hour and a half from both Baltimore and Washington, DC. If you’re driving from DC, you’ll cross the Chesapeake Bay Bridge, and the pace will start to change. Plan to arrive by 1pm so the whole afternoon is yours.
A dozen roses will be waiting in your cottage, along with six house-made chocolate truffles. When berries are in season, we swap the truffles for chocolate-covered strawberries. Unpack slowly, open the porch door, and let the stress fall away.
Day Two: Breakfast, a Picnic, and a Night Out
Call us when you wake, and we’ll bring a gourmet breakfast to your cottage between 8:30 and 10am. Our menu changes with the seasons and what’s growing in our garden. Afterward, head into town for a few of the date ideas above.
While you’re out, we’ll tidy your cottage and deliver a picnic lunch. Spend the afternoon however you like: soak in the Japanese tub, read a book on the screened porch, or take a well-earned nap. That evening, return to town for a four-course wine-tasting dinner at The Kitchen at the Imperial. Couples who would rather stay in can choose our Secret Getaway package instead.
Day Three: A Slow Morning and a Late Checkout
Breakfast arrives at your door once more, and on mild mornings it tastes even better on your private patio. Check-out isn’t until noon, so there’s time for one last walk through the gardens. Many couples tell us this is the morning they start planning their next visit.
Why Is Doing Nothing One of the Most Romantic Things to Do in Maryland?
Guests often arrive with a list of plans for their stay. By the second day, many of those plans have softened, and a slow afternoon at our inn wins out. We take that as a compliment.
Our 35-acre estate makes doing nothing easy. Wander the gardens and walking paths, read on your cottage porch, or settle in by the fire. Select rooms and cottages add wood-burning fireplaces and soaking or jetted tubs. In the afternoon, come back for tea and something sweet. Couples who want to fully unplug can add an in-room massage for two.
Which Brampton 1860 Packages Fit Your Occasion?
Our packages handle the planning so that you can focus on each other. Each one suits a different occasion:
- Wine Country Date Night Special: A tasting flight and cheese platter at Crow Vineyard, plus a picnic dinner for two delivered to your room. Available Sun–Thu.
- Treasured Romance Cottage Package: The three-day cottage itinerary above, with roses on arrival and a four-course dinner in town.
- Secret Getaway: Your own secret hideaway for two nights. Park the car, close the cottage door, and stay tucked in together while we deliver every meal.
- “I Do” Proposal Package: Red rose bouquet, champagne, and silk rose petals on your bed. We arrange it all before the big moment.
Pricing and dates shift with the seasons, so we keep the latest details for each package on our Specials page. Not sure which one suits your plans? Give us a call at 410-778-1860, and we’ll help you choose.
When Should Couples Plan a Romantic Weekend on Maryland’s Eastern Shore?
There’s no bad time for a romantic getaway on Maryland’s Eastern Shore. Each season offers something different, depending on what you enjoy doing together.
- Spring fills our gardens with blooms and brings the Chestertown Tea Party Festival downtown in late May.
- Summer is for the river, with sailing, kayaking, and long evenings on the porch.
- Fall brings foliage, harvest wines, and the year’s first fireside nights.
- Winter is our quietest season and a favorite for couples who want the place nearly to themselves. Dickens of a Christmas turns downtown Victorian on the first weekend of December. Midweek stays, Sun–Thu, are especially peaceful this time of year.
Frequently Asked Questions About Romantic Things to Do in Maryland
How far is Chestertown, MD from DC, Baltimore, Philadelphia, and NYC?
Brampton 1860 is about an hour and a half from Baltimore and Washington, DC. Philadelphia is roughly two hours away, and New York City is about three hours without stops.
How many days should couples spend in Chestertown?
We recommend at least two nights for a romantic weekend in Maryland. Three or more days gives you time to explore town, visit a vineyard, and still leave whole afternoons open.
Can Brampton 1860 help plan a proposal?
Yes, our “I Do” Proposal Package sets the scene with roses, champagne, and rose petals. Tell us your plans when you book, and we’ll have everything ready before the moment.
Plan Your Chestertown Escape
The most romantic things to do in Maryland don’t require a packed schedule. They ask for a little time, a good porch, and someone you’d like to share it with. Winter is one of our favorite seasons to welcome couples. The river goes quiet, and the fireplaces come on.
Reserve your cottage at Brampton 1860, and we’ll take care of the rest.
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