The Best Classic comfort food in Chestertown, Maryland

"The Prickly Pickle is a charming food establishment located at 827 High Street in Chestertown, Maryland. Known for its delicious and unique pickle-themed menu, this restaurant offers a variety of mouthwatering dishes that are sure to satisfy any pickle lover's cravings. Whether you're in the mood for a classic pickle sandwich or want to try a more creative pickle-infused dish, The Prickly Pickle has something for everyone. Come visit us and experience the delightful flavors of our pickled creations in a cozy and inviting atmosphere."

Stam's Luncheonette is a charming food establishment located at 215 High Street in Chestertown, Maryland, United States. This historic lunch counter offers a variety of classic American lunch and breakfast staples, as well as fountain sodas and delicious house-made ice cream and sundaes. The flavors of ice cream rotate regularly, so be sure to visit the shop to see the current offerings. Situated in a building that once housed a 19th-century pharmacy until 2016, Stam's Luncheonette is now a beloved landmark in downtown Chestertown. Come experience the nostalgia and taste the delicious flavors at this quaint eatery.

The FREEZE is a popular food institution located at 717 Washington Avenue in Chestertown, Maryland. This cozy restaurant offers a variety of delicious frozen treats and comfort foods, making it a favorite spot for locals and visitors alike. With a welcoming atmosphere and friendly staff, The FREEZE is the perfect place to satisfy your cravings and enjoy a tasty meal with friends and family. Whether you're in the mood for a classic milkshake, a juicy burger, or a refreshing ice cream cone, The FREEZE has something for everyone to enjoy. Come stop by and experience the mouthwatering flavors and warm hospitality that make The FREEZE a must-visit destination in Chestertown.

Welcome to Jellyfish Joel's Beach Bar, located at 22170 Great Oak Landing Road in Chestertown, Maryland, United States. Our bar is not just a place to grab a drink, but a destination for boaters and beach lovers alike. At Jellyfish Joel's, we take pride in caring for your boat with passion and attention to detail. Our newly renovated on-premise accommodations offer comfortable rooms with amenities such as a mini fridge, private bathroom, and access to ice & coffee stations. Guests can enjoy free parking, free Wi-Fi, and access to the beach, outdoor pool, golf course, and more during their stay. The Lodge is open year-round and conveniently located for local events.