Food & Dining at our Historic Maryland Bed and Breakfast

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, November 24, December 15, 2024, January 26 and February 23, 2025 – 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.

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!
• Save 50% off your fourth night!**

$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.

**Discount applied to the room rate only of the least expensive night. Applicable to new reservations only.

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.

The perfect way to start a romantic getaway. Our charcuterie platter includes the following:

• A plate of cured meat
• Olives
• Pickled vegetables
• Baguette

$59

A vacation is a perfect way to celebrate a special occasion such as anniversaries, promotions, birthdays, and more. For an extra special surprise, we are more than happy to help. We can have a delicious, homemade celebration cake waiting in your room upon arrival. It’s the perfect way to elevate your stay with us without interrupting your travels and planning because we take care of it all for you. Whatever the occasion, make it a memory that you and your loved one won’t soon forget. Choose from Cake Flavors: Chocolate, Vanilla, and Carrot.

$30

A sweet surprise of eight delicious, home-made and gluten-free coconut macaroons.

$20

For a big WOW factor consider this big romantic gesture waiting in your room for an unexpected surprise:

• A bouquet of roses perfectly arranged in a tall vase. If there is a color preference let us know.
• Six decadent hand-crafted dark chocolate truffles or chocolate covered strawberries.
• A note from you. Let us know your message, we’ll take care of the rest!

$109

Roses ordered between February 4-February 18 & April 20 and April 29-May 15 may be subject to an additional fee based on market prices.

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 $115 per person plus tax. Gratuity not included.

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