Clovelly Vineyards (Chestertown, Maryland)
Clovelly Vineyards in Chestertown, Maryland, offers a picturesque escape with its stunning views of the Chester River and lush vineyards. This family-owned vineyard is known for its commitment to sustainable farming practices and producing high-quality wines that reflect the unique terroir of the region. Visitors can enjoy wine tastings, vineyard tours, and special events throughout the year. The historic town of Chestertown adds to the charm, with its colonial architecture and vibrant cultural scene. CliftonCab provides convenient and comfortable transportation services, ensuring you can explore Clovelly Vineyards and the surrounding area with ease. Whether you’re a wine enthusiast or simply looking for a relaxing day trip, CliftonCab guarantees a pleasant and reliable journey. Experience the best of Maryland’s wine country with CliftonCab’s exceptional service.
Restaurants near Clovelly Vineyards
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The Lemon Leaf Café
American
337 High St, Chestertown, MD 21620
(410) 778-2233
The Lemon Leaf Café is a beloved local spot offering classic American dishes with a focus on fresh, locally sourced ingredients. The cozy atmosphere and friendly service make it a favorite among both residents and visitors.

Monday
8:00 AM – 8:00 PM
Tuesday
8:00 AM – 8:00 PM
Wednesday
8:00 AM – 8:00 PM
Thursday
8:00 AM – 8:00 PM
Friday
8:00 AM – 9:00 PM
Saturday
8:00 AM – 9:00 PM
Sunday
8:00 AM – 8:00 PM
The Fish Whistle
Seafood
98 Cannon St, Chestertown, MD 21620
(410) 778-3566
The Fish Whistle offers waterfront dining with a menu featuring fresh seafood and classic American dishes. The beautiful views of the Chester River and relaxed ambiance make it a perfect spot for a leisurely meal.

Monday
11:00 AM – 9:00 PM
Tuesday
11:00 AM – 9:00 PM
Wednesday
11:00 AM – 9:00 PM
Thursday
11:00 AM – 9:00 PM
Friday
11:00 AM – 10:00 PM
Saturday
11:00 AM – 10:00 PM
Sunday
10:00 AM – 9:00 PM
Luisa’s Cucina Italiana
Italian
849 Washington Ave, Chestertown, MD 21620
(410) 778-5360
Luisa’s Cucina Italiana serves authentic Italian cuisine in a warm and inviting setting. The extensive menu and excellent wine selection make it a great choice for a special night out or a casual dinner.

Monday
Closed
Tuesday
11:00 AM – 9:00 PM
Wednesday
11:00 AM – 9:00 PM
Thursday
11:00 AM – 9:00 PM
Friday
11:00 AM – 10:00 PM
Saturday
11:00 AM – 10:00 PM
Sunday
11:00 AM – 9:00 PM
Barbara’s on the Bay
American
20855 Bayside Ave, Rock Hall, MD 21661
(410) 639-2263
Located a short drive from Chestertown, Barbara’s on the Bay offers a delightful dining experience with scenic views of the Chesapeake Bay. The menu features a variety of American dishes with a focus on fresh, local ingredients.

Monday
Closed
Tuesday
11:00 AM – 8:00 PM
Wednesday
11:00 AM – 8:00 PM
Thursday
11:00 AM – 8:00 PM
Friday
11:00 AM – 9:00 PM
Saturday
11:00 AM – 9:00 PM
Sunday
10:00 AM – 8:00 PM
Blue Heron Café
American
236 Cannon St, Chestertown, MD 21620
(410) 778-0149
Blue Heron Café is a charming eatery offering a menu of fresh, seasonal dishes in a cozy setting. The café’s focus on local produce and creative cuisine makes it a standout dining destination in Chestertown.

Monday
Closed
Tuesday
11:00 AM – 9:00 PM
Wednesday
11:00 AM – 9:00 PM
Thursday
11:00 AM – 9:00 PM
Friday
11:00 AM – 10:00 PM
Saturday
11:00 AM – 10:00 PM
Sunday
11:00 AM – 8:00 PM
Osprey Point Restaurant
American
20786 Rock Hall Ave, Rock Hall, MD 21661
(410) 639-2194
Osprey Point Restaurant, located near Chestertown in Rock Hall, offers fine dining with beautiful waterfront views. The menu features a range of American dishes, from seafood to steaks, all made with fresh, local ingredients.

Monday
Closed
Tuesday
Closed
Wednesday
5:00 PM – 9:00 PM
Thursday
5:00 PM – 9:00 PM
Friday
5:00 PM – 9:00 PM
Saturday
5:00 PM – 9:00 PM
Sunday
5:00 PM – 8:00 PM
Cafe Sado
Asian Fusion
870 High St, Chestertown, MD 21620
(410) 778-5300
Cafe Sado offers a unique blend of Asian fusion cuisine in a modern and relaxed setting. The menu includes sushi, Thai dishes, and other Asian-inspired creations, making it a popular choice for diverse palates.

Monday
Closed
Tuesday
11:30 AM – 9:00 PM
Wednesday
11:30 AM – 9:00 PM
Thursday
11:30 AM – 9:00 PM
Friday
11:30 AM – 10:00 PM
Saturday
11:30 AM – 10:00 PM
Sunday
11:30 AM – 9:00 PM
Lemon Leaf Café
American
337 High St, Chestertown, MD 21620
(410) 778-2233
Lemon Leaf Café is a staple in Chestertown, known for its homestyle American cooking and welcoming atmosphere. The café’s commitment to using fresh, local ingredients makes it a favorite among both locals and visitors.

Monday
8:00 AM – 8:00 PM
Tuesday
8:00 AM – 8:00 PM
Wednesday
8:00 AM – 8:00 PM
Thursday
8:00 AM – 8:00 PM
Friday
8:00 AM – 9:00 PM
Saturday
8:00 AM – 9:00 PM
Sunday
8:00 AM – 3:00 PM
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Dulles Airport
Reagan Airport
Baltimore Airport
The Lemon Leaf Café
The Fish Whistle
Luisa’s Cucina Italiana
Barbara’s on the Bay
Blue Heron Café
Osprey Point Restaurant
Cafe Sado
Lemon Leaf Café
Wedding Venues near Clovelly Vineyards
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Clovelly Vineyards
Vineyard
301 Clovelly Ln, Chestertown, MD 21620
(443) 480-0622
Clovelly Vineyards provides a stunning vineyard setting for weddings, with breathtaking views of the Chester River and lush vineyards. The venue’s natural beauty and rustic charm create an unforgettable backdrop for any wedding.

Generic Pricing
$6,000 – $15,000
Capacity
Up to 200 guests
Website
www.clovellyvineyards.com
Brittland Estates
Estate
211 Britland Farm Ln, Chestertown, MD 21620
(410) 810-7591
Brittland Estates offers elegant and picturesque estate settings for weddings, with beautiful gardens and historic charm. The venue’s spacious grounds and luxurious accommodations make it ideal for grand celebrations.

Generic Pricing
$10,000 – $25,000
Capacity
Up to 300 guests
Website
www.brittlandestates.com
The Inn at Huntingfield Creek
Bed and Breakfast
4928 Eastern Neck Rd, Rock Hall, MD 21661
(410) 639-7779
The Inn at Huntingfield Creek offers a charming bed and breakfast setting for weddings, with beautifully landscaped gardens and cozy accommodations. The venue’s intimate and serene atmosphere makes it perfect for smaller, more personal celebrations.

Generic Pricing
$5,000 – $12,000
Capacity
Up to 150 guests
Website
www.huntingfield.com
The Brampton Inn
Historic Inn
25227 Chestertown Rd, Chestertown, MD 21620
(410) 778-1860
The Brampton Inn offers a historic inn setting for weddings, with elegant interiors and beautiful grounds. The venue’s classic charm and sophisticated ambiance create a perfect backdrop for timeless weddings.

Generic Pricing
$7,000 – $18,000
Capacity
Up to 200 guests
Website
www.bramptoninn.com
The Grand Hotel
Historic Hotel
210 High St, Chestertown, MD 21620
(410) 778-2100
The Grand Hotel provides a historic hotel setting for weddings, with beautiful event spaces and excellent service. The venue’s grandeur and historic charm make it a popular choice for elegant weddings.

Generic Pricing
$8,000 – $20,000
Capacity
Up to 250 guests
Website
www.thegrandhotelchestertown.com
Wilmer Park Pavilion
Pavilion
413 S Cross St, Chestertown, MD 21620
(410) 778-0500
Wilmer Park Pavilion offers a scenic pavilion setting for weddings, with beautiful views of the Chester River. The venue’s open-air design and picturesque location make it ideal for outdoor celebrations.

Generic Pricing
$3,000 – $10,000
Capacity
Up to 200 guests
Website
www.chestertown.com
White Swan Tavern
Historic Inn
231 High St, Chestertown, MD 21620
(410) 778-2300
White Swan Tavern provides a historic inn setting for weddings, with charming interiors and a cozy atmosphere. The venue’s historic elegance and intimate setting make it perfect for smaller, more personal weddings.

Generic Pricing
$4,000 – $12,000
Capacity
Up to 100 guests
Website
www.whiteswantavern.com
The White House Farm
Farm
24534 Chestertown Rd, Chestertown, MD 21620
(410) 778-2641
The White House Farm offers a rustic farm setting for weddings, with beautiful landscapes and charming farm buildings. The venue’s relaxed and natural ambiance makes it a perfect choice for rustic and country-style weddings.

Generic Pricing
$6,000 – $15,000
Capacity
Up to 200 guests
Website
www.thewhitehousefarm.com
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Airport Taxi Transportation near Clovelly Vineyards
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