Escaping on a midweek getaway feels a little “naughty.” Getting away on the weekend is expected. Generally, you’re not working and can choose your own agenda on Saturdays and Sundays. But when you whisk away midweek, well, it’s just special, almost magical. Your coworkers are rushing around the office from meeting to meeting. You, on the other hand, are slowly sipping a hot cup of coffee on a quiet porch, listening to the gentle sounds of nature.
An Eastern Shore escape to Brampton 1860, is the best. You can wander through the quiet, historic streets of Chestertown. Or if you truly want to unwind, wander through our gardens and trails. Breathe in the fresh air. Watch the breeze ripple through the leaves. Relax in a hammock or snuggle under the covers of your luxurious bed. Can’t you just feel the stress melting away? At Brampton 1860, we believe a midweek getaway isn’t just a break, it’s a little slice of midweek magic. And we have a great itinerary for your midweek escape.
Act now and receive additional savings!
Midweek Autumn Escape Special
Stay 3 consecutive nights Sunday-Thursday and enjoy 30% off your third night
Offer valid for 3-night minimum stays, Sun–Thu now thru Nov 25, 2025. Savings applied to the least expensive night.
New reservations only. Not available with other specials on third-party sites.
Why Midweek Is the Best Time to Visit
Midweek travel is our best-kept secret on Maryland’s Eastern Shore. When you visit during the week, the pace slows, the crowds fade, and you can truly relax. It’s the best time to connect with each other and recharge before you get back to your day-to-day.
- You’ll find easier reservations at local restaurants. We’re happy to recommend some of our favorites.
- Experience quieter trails for hiking.
- You can also spend more time lingering at one of our wineries or galleries.
- The best part? Our weekday rates make a midweek getaway an incredible value without sacrificing comfort or experience.
At the inn, we add even more charm to your stay. Imagine fresh-baked pastries, savory selections, and coffee waiting for you each morning. Afternoons spent wandering through our 35 acres of blooming gardens. It’s peaceful, private, and entirely yours. In the evening, cocktails and soft music in the Maison de Lumière lounge. Yes! It’s exactly what a romantic midweek getaway should be.
Let’s get started.
Day 1 | Arrive, Unwind, and Savor the Moment
You’ll know your escape has begun the moment you turn onto our tree-lined drive. Even the air feels different here. It’s softer, quieter, almost suspended in time.
If you’re coming from Baltimore, D.C., or even New York City, plan to arrive by early afternoon. Stop for lunch along the way or enjoy a scenic drive down the Eastern Shore. Once you arrive, we will welcome you with warm smiles and perhaps a glass of wine or cider.
Settle into your room or private cottage, plop down in a comfy chair or your bed and sigh, releasing your stress. As the sun sets, wander into Chestertown for dinner at Watershed Alley or one of our favorites, The Kitchen at the Imperial. Afterward, return for a quiet conversation while snuggling by the fire.
Want to add something extra to your first night? Try one of our enhancements. Roses and chocolates are always a great choice. Little touches like these make your Eastern Shore escape even more memorable.
Let’s continue with your midweek itinerary.
Day 2 | Explore the Eastern Shore at Your Pace
The beauty of a midweek getaway is that there’s no schedule. Wake up slowly, enjoy a chef-prepared breakfast, and let the day unfold naturally. Speaking of breakfast, prepare yourself for the best one on Maryland’s Eastern Shore. Our chef and kitchen staff offer freshly made options that are delicious and filling. You’ll also enjoy chatting with other guests and owners, Dave and Hilari. It’s the perfect recipe for a relaxing morning.
Explore the Outdoors
If you love the outdoors, we’ll point you toward some of our favorite nearby trails.
- Eastern Neck National Wildlife Refuge: Some of the best nature trails are found here. In the fall, you’ll see some spectacular foliage. Regardless of when you visit, you’ll likely see some migratory birds, bald eagles, and other natural wildlife.
- Tuckahoe State Park: Another popular spot for hiking with over 20 miles of trails. It’s the perfect choice if you like trails along a bubbling creek. We can even pack a gourmet picnic for you to enjoy under the shade of the trees.
- Blackwater National Wildlife Refuge: This is THE place to be for bird watching. They have reported seeing over 200 varieties of birds. These trails are also teeming with other wildlife.
Indulge in Indoor Activities
Prefer something a little more leisurely? Take a stroll through Chestertown’s historic district. Wander the cobblestone streets and see our centuries-old buildings. They tell stories of another time. Pop into RiverArts Gallery or browse our local boutiques for unique, handmade goods.
Twigs and Teacups
📍 111 South Cross Street, Chestertown, MD (directions)
This is our favorite gift shop in town. You’ll find smart, small gifts, toys, candles, and soaps. Hilari often stops in to browse. She’s purchased several things for the inn, including tea towels, holiday ornaments, books, and fun serving dishes. When you visit, their resident cat will help you as you check out. What Hilari really loves is their building restoration, which was completed a couple of years ago. That in itself is worth a visit.
Bespoke Chocolate
📍 207 S. Cross Street, Chestertown, MD (directions)
Seriously? This is a must-visit on the itinerary. We absolutely love their sweet treats and delicious chocolates. In fact, we feature them at our inn. They make decadent truffles, bon bons, dipped fruit, cordials, plus 16 flavors of fudge. All are hand-made with the finest ingredients. Yum!
The Finishing Touch
📍 311 High Street, Chestertown, MD (directions)
We love this place, and all our artwork and collections have been framed here. They specialize in custom frames. However, they also offer fine art, prints, and photography. You’ll also find historical maps and Chesapeake Bay-inspired decor. It’s a great place to choose a special gift — and to visit Sabre and Heckles, the resident dog and cat.
Additional Shops
- Chester River Wine and Cheese Co.: Are you a foodie? This is THE spot for you. Their shop offers a little bit of everything, but all gourmet. Items you find here make wonderful gifts that your friends and family will love. We think owners Jon and Jennifer are great.
- Walnut & Wool: A great shop for vintage or new clothing and home decor. It’s very eclectic, filled with unique items. They also do their own furniture refinishing. You’ll find pieces you and your friends will love.
- Silver Lining Jewelry: Looking for a gift of bling? Stop in and browse their extensive selection of sterling silver pieces. Best part — they’re all at a great price, too. You may see Hilari sporting some of their creations.
- The Bookplate: This is definitely one of our hidden gems. In our world of “everything digital,” this place has the wonderful aroma of actual history and books. You know, the kind you hold in your hand. Those favorites that are literally “page turners.” They sell almost any type of gently used books you can imagine. Can’t find what you want? Keke, the cat, can help.
Sip, Savor, and Slow Down
In the afternoon, head to one of our local vineyards, like Crow Vineyard. They are our “partners in wine.” If you opt for our Wine Country Date Night Special, a tasting flight and cheese platter at Crow Vineyard is included. Take some time to stroll around the property and see their grass-fed Angus herd. Select a bottle or two to take home as gifts or to enjoy at home.
If you prefer staying in Chestertown, Casa Carmen Wines is a lovely choice. It’s a cozy tasting room perfect for sipping traditional wines and engaging in warm conversation.
Back at the inn, unwind with tea on the veranda, a soak in your private tub, or perhaps an in-room massage (be sure to schedule it ahead). Dinner can be as simple or as elegant as you’d like. We’ll happily make recommendations or reservations for you. One of our absolute favorites for casual dining is Bad Alfred’s. Located in the heart of Chestertown, they offer house-made spirits and wood-fired pizzas. You’ll love their Raspberry Blonde (best thing on a hot summer’s day!).
By evening, you’ll understand what we mean when we talk about midweek magic. The quiet feels deeper. The stars seem brighter. Time, somehow, moves more slowly even with all the adventures of the day.
Day 3 | Slow Mornings and Sweet Goodbyes
Before you check out, linger a little longer. Sip one more cup of coffee, take one more stroll through the garden, and let yourself sink into the rhythm of this place.
If you missed a shop yesterday, head into Chestertown to pick up a little something to remind you of your stay. The memories it brings may be just what you need back in your day-to-day hustle.
And if you’re already thinking, “I wish we could stay just one more night,” you’re not alone. Many guests extend their midweek getaway because, well, once you’re here, it’s hard to leave.
Tips for Planning Your Midweek Getaway
A little planning goes a long way in making your trip seamless and stress-free.
- Book directly through our website for the best rates and most flexible options.
- Ask about enhancements like flowers, wine, or chocolate-covered strawberries to make your stay more romantic.
- Pack casual layers. Maryland’s Eastern Shore weather can shift, and you’ll want to be comfortable for exploring or relaxing outdoors.
- Check our packages page for current specials, including discounts for multi-night midweek stays.
- If you’d like even more inspiration, read our companion post, The Benefits of Traveling Midweek. It’s full of reasons why midweek travel feels so restorative and special.
Your Midweek Story Awaits
Every guest who stays with us writes a little part of Brampton 1860’s story. Midweek visitors, though, often tell us they feel something extra. It’s a calm that stays with them long after they leave. Maybe it’s the quiet. Maybe it’s the way the light filters through the trees. Or maybe it’s simply having the space to reconnect with yourself and the one you love.
If you’ve been waiting for the right moment to get away, this is it. Pack light, bring your curiosity, and let us handle the rest. This midweek getaway for couples or solo travelers is just what you need to conquer your workweek woes.
So, what are you waiting for? Your midweek escape is waiting at Brampton 1860 — and we can’t wait to welcome you!
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