Food & Dining at our Historic Maryland Bed and Breakfast

Dining Under the Stars offers a captivating night open-air dining experiences set amidst the historic charm of the 35-acre country estate of the Brampton 1860, in Chestertown, Maryland.

Guest Chefs craft an indulgent multi-course feast that spotlights the best of Eastern Shore cuisine. No two events are alike; each inspired by a theme at every level – from cuisine, tablescape, to live music, to wines and cocktails, you can always expect an elevated farm-to-table experience, with extraordinary presentations, while staying true to the essence of the area.

Each evening starts in the garden, with a refreshing welcome cocktail and delightful appetizers to tantalize the taste buds. The night’s highlight arrives with a multi-course dinner served beneath the stars on the Renaissance Garden terrace. To enhance the culinary experience, a range of wines will be offered for sale to complement each dish.

July 30 – From Land and Sea MENU

August 20 – Sizzlin’ Gourmet BBQ MENU

Brampton’s exclusive dinner parties require advance booking. Price is $95* per person, excluding taxes and gratuity. Guests of the Inn enjoy 10% off dining tickets and decadent breakfast the next morning. If you would like to book the event without booking a room reservation, please click here to make your reservation online or give us a call at 410-778-1860.

*Please note that price is per person and we require advance notice of at least 7 days to reserve your seat.

Join us for an elegant afternoon of fine food and drink, and wonderful conversation!

Our pastry chef’s creations of decadent sweet and mouth-watering savory bites are paired with a hand-picked selection of fine Harney & Sons Teas including iced tea in the warmer months. Enjoy as you and your companions spend a lovely afternoon in the peaceful elegance of the Brampton.

Available June 23, July 28, August 25, September 22 and October 27, 2024 – 2:00 – 3:30 pm and seating is at 2:00 pm.

*Please note, due to the nature of this event, only regular and vegetarian options are available.

**To purchase tickets for the event without an overnight stay, either call us at 410-778-1860 or purchase online here.

Dine in the comfort of your room or the dining room with these delicious homemade picnic dinners for two.

Entree Options:

• Chicken Taco Salad
• Stuffed Peppers
• Grilled White Veggie Pizza

Each dinner includes mixed green salad, crusty bread, a delectable seasonal dessert, and a bottle of red or white wine!

Let us know which entrée you would like when booking.
$89

The perfect start to a relaxing getaway in Maryland. Our cheese board enhancement includes:

• A selection of four different kinds of cheese
• Olives
• Crackers
• Baguette
• Fresh fruit

$59

Homemade hummus with a splash of EVOO and seasonal vegetables is the perfect snack waiting for you when you didn’t have time to grab a bite to eat before getting on the road. It’s good for you too.

$25

Sweet surprise:

• Add a sweet treat for your sweetheart with a box of 16 assorted artisan chocolate truffles from local chocolatier, Bespoke Chocolate, beautifully packaged and waiting for you in your room.
• Add a note from you. Let us know your message, we’ll take care of the rest!

$29

Escape and relax in the upper Eastern Shore haven of Brampton 1860, the perfect destination for couples or families seeking a traditional Thanksgiving retreat November 27- December 1. Explore the charming streets of our historic town, and you’ll find yourself surrounded by breathtaking natural beauty, family-owned businesses, and a thriving art scene. Click here to read all of the details! During your stay, you’ll be treated to:

• Champagne, local hand-crafted chocolate and live music welcome on arrival day
• A lavish Thanksgiving Day feast with a glass of Crow Vineyard wine (additional wine available for sale by the glass or bottle)
• A live musician playing during Thanksgiving dinner
• $60 Chestertown Cash Gift Certificate to shop the downtown boutique shops
• A 3-course locally-sourced gourmet breakfast served each morning
• Decadent tea-time treats and homemade cookies are available daily – we’ll have something extra on Friday and Saturday!

$325 per couple, plus lodging and taxes.
*Package must be reserved 4 days in advance and requires a 4-night minimum stay, November 27 – December 1, 2024, additional nights may be added. Restrictions may apply, based on availability.

Celebrate the most magical time of year at your favorite inn! Join us for a special Christmas Day dinner. 3 courses including prime rib (a salmon option is also available) and all the accompaniments and a glass of wine for just $125 per person plus tax. Gratuity not included.

Book online or call (410) 778-1860 to book your Christmas dinner and lodging reservations.

Ring in the New Year Brampton 1860 style December 30th-January 1st! Experience Eastern Shore elegance on a 2-night, 3-day getaway complete with:

• Guests will be greeted with a glass of Champagne upon arrival on Monday
• On Tuesday, enjoy a traditional New Year’s Eve early Dinner at the Inn at 2 pm
• Then celebrate the arrival of the new year in style with a 1940’s inspired cruise aboard the historic Chester River Packet on Tuesday 4 pm – 6 pm. While onboard, guests will enjoy an assortment of decadent cheeses, desserts and drinks (cash bar) and listen to live music while enjoying exceptional views of Chestertown’s historic waterfront, sunset and all-around good times
• Retire back to the Inn and uncork a bottle of bubbly, teamed with a delicious snack box assortment to ring in 2025
• Delicious, full breakfast prepared with fresh local ingredients each morning!

*Package must be reserved 3 days in advance and requires a 2-night minimum stay, December 30th-January 1st, additional nights may be added. Restrictions may apply, based on availability.