Eastern Shore Vacation Rentals

The Berlin Farmers Market
2023-06-11 08:00 - 2023-09-24 14:00 UTC
Only market in the heart of downtown Berlin featuring more than 30 farmers, bakers, food cultivators and more. Shops in the downtown also open early on Sundays.
Live music starts at 10am. Free to attend, free to park!

Farms:

Bennett Orchards: Peaches and Blueberries (in season only)
BayBees Farm: Honey
Assateague Farm: Flowers
Bratten Farm: Locally Grown Produce
Cross Farms: Locally Grown Produce
(Shawn Cross, Market Manager)
Goat Plum Tree Farm: Lettuces, in season fruit and mushroom logs
Splendid Earth Acres Farm: Locally Grown Produce
The Bay Mushrooms Farm: Variety of locally grown mushrooms
6 Kings Farm: Lamb and beeswax products
The Good Farm: Locally grown plants and herbs
Beckys Beanz: Locally grown plants, garden flowers, produce
Marshall Creek Farm: Goat milk items and hand-made wool products
Truitt Farm: Handcrafted hot sauces from their pepper farm

Featuring:

The Buzz Meadery: Variety of locally made mead
Mandala Pies: Pies made from scratch
Little Green Witch Apothecary Teas
Beehouse Soap
Iron Skillet Coffee
Una Bella Salute: Downtown shop offering olive oils and vinegars
baked dessert café: Downtown bakery offering desserts, breads, granola, more
Del’Vecchios Bakery: Variety of baked goods, cookies, breads, more.
Home Canning Classics: Jams, jellies, pickled items, more
Honey Water Candles: Soy candles from local Berlin shop
Lyon Rum: Variety of rum distilled in Easton MD
Bleached Butterfly: Flower arrangements from local Berlin shop
KMBelz Pottery: Locally made pottery
Mother Flowers: Flowers
Sweet Tater Treats for Animals: Locally made for a variety of pets
Clare’s Nutty Concoctions
The Street Kitchen: Food Truck
Krave Gluten Free Bakery
Gather Bakery: Alfajores, Savory Biscuits made from scratch
Pearl Moon Face Painting
Gilberts Provisions: Fresh baked bread, breakfast burritos

Sail on the Skipjack Nathan (June 10th)
2023-06-10 13:00 - 15:00
Nathan sails from May through October. Each sail is two hours long and generally includes an oyster dredging demonstration. Sails are unique depending on wind, weather, captain and crew.
Advance reservations are recommended and accepted online use the link below, until midnight of the day before the sail. We carry up to 20 passengers per trip and the boat leaves the dock promptly on schedule.
Booking – Skipjack Nathan (skipjack-nathan.org)

Adults
Children Aged 4–12
Children Under Age 4

$40.00
$15.00
Free

Tall Ship Kalmar Nyckel Sails in Cambridge (June 4th)
2023-06-04 10:00 - 12:30
Come sail away with Kalmar Nyckel for a 2.5-hour sail and have an adventure of a lifetime!
The Tall Ship of Delaware returns to Cambridge, MD on Friday, June 2 through Sunday, June 4. Discover the remarkable story behind Kalmar Nyckel, a full-scale replica of the merchant ship that brought Swedish settlers to North America in 1638.
Day sails on the Kalmar Nyckel offer a unique, hands-on experience where adventure and education come together. You can haul lines, set sails, and hear tales from the crew, or simply relax and enjoy the ship. Kids will enjoy a scavenger hunt and pirate story (costumes welcome).
Tickets are limited and available online (KalmarNyckel.org/explore) or by calling 302.429.7447 for $65 per adult and $40 per child 12 and younger. Advance reservations are highly recommended. The schedule is weather dependent.

Kent Island Farmers’ Market
2023-06-03 15:30 - 2023-11-25 18:30
With over 30 local vendors at KENT ISLAND FARMERS’ MARKET at Cult Classic Brewery Year-round every Thursday. Hours 3:30- 6pm through Spring, Summer and Fall. January through March 3:30- 5:30. Experience local selection of seasonal fruits and vegetables. Hand crafted jewelry, crafts, home decor and more! Homemade baked goods, beauty products, local breweries and restaurants all at your fingertips.

Annapolis Pride Parade & Festival
2023-06-03 12:00 - 19:00
With over 6,000 people in attendance, 2019 launched the Inaugural Annapolis Pride Parade & Festival– a visual dreamscape of the human spirit at its best. People, children, and pets of every walk of life dress in their rainbow finest and line the sidewalks of West Street to witness a dazzling parade of floats, dancing spirit dragons, musicians, motorcycles, and more. It was a day of pure love and joy – many community members couldn’t believe their eyes at the crowds.

PARADE
Time: Begins at Noon on June 3rd
Where: West Street, Amos Garrett Boulevard to Calvert Street, Clay Street
FESTIVAL
Time: 12 pm to 7 pm
Where: West Street, between Calvert Street and Church Circle, The People’s Park, and adjacent parking lots

St. Michaels Brewfest 2023
2023-06-03 12:00 - 16:00
On June 3rd, from 12:00 pm – 4:00 pm come out to the St. Michaels Brewfest 2023!
They offer Three Pouring Venues, Over A Dozen Breweries, Art, Glassware, Food, and more!
Tickets are limited and can be purchased on the website below, Offering General admission and a VIP cruise tickets are still available!

St. Michael’s Brewfest – St Michaels Brewfest 2023

Sail on the Skipjack Nathan (June 3rd)
2023-06-03 12:00 - 15:00

Tall Ship Kalmar Nyckel Sails in Cambridge (June 3rd)
2023-06-03 10:00 - 12:30

Easton Farmers Market
2023-06-03 08:00 - 2023-12-16 13:00
From local produce growers to watermen, from bakers to crafters and local artisans, the Easton Farmers Market provides an entire meal, home décor and unique gift items in a friendly and festive environment. The market is open every Saturday from April 15 to December 16, 2023 at 8 a.m. to 1 p.m. Live music starts at 10:30 a.m.
Parking is available for free directly across the street from the market via Brewers Lane. The market is a walkable distance to shops, galleries, restaurants, and the historic Avalon Theatre.

Chesapeake Bay Champagne Sunset Sail
2023-06-02 17:30 - 19:30
Looking to go sailing at sunset while sipping champagne? This is the sunset champagne charter for you!
Come join us for a relaxing 2 hour cruise near Annapolis. Your St Michaels MD sail boat ride includes a personalized tour with our first class captains & crew on all our boating trips including our romantic sunset champagne cruise. Unique, upscale, and exclusive, the luxury sailing yacht Selina II limits her passengers to just 6 guests for an intimate taste of the history of sailing. With Freshly varnished mahogany and brightly polished brass let the premier charter boat St Michaels, MD help you sail into another time and place.
Per person: Starts at $115
Private charter minimum 2 people: Starts at $675

Max 6 passengers: Must be 21 or older to consume adult beverages.
Check-in time: 15 minutes prior to departure
Children: Please note that while this excursion is primarily an adult experience, well-behaved children are more than welcome to join in on the fun. The Coast Guard considers every kid no matter how young or how little to be a passenger, and as such require their own ticket.
Parking: Free parking where we are parked at the Harbour Inn, 101 N Harbor Road, St Michaels MD 21663. If there are no spaces available, then there is parking on the side streets and along the waterfront down past where the work boats tie up.

St. Michaels Yacht Wine Tasting Cruise
2023-06-02 15:00 - 2023-10-29 17:00
Enjoy a truly unforgettable wine tasting experience on the Chesapeake Bay with Sail Selina II. Our 2-hour St Michaels, MD wine tasting cruises are the perfect way to indulge in the basics of wine tasting while taking in breathtaking views of one of the most picturesque waterfronts in America. With limited availability for just six guests per excursion, our wine cruises are perfect for a special girls night out or with your sweetheart.
Experience the rich aromas and flavors of 3 reds and 3 whites, including a stunning Italian Pinot Grigio that will transport your senses to the breathtaking vineyards of Italy. Capt Iris lovingly handpicks a constantly changing selection of global wines, ensuring that each excursion with us is a unique, personalized adventure that you’ll remember for years to come.

$95 per person, minimum 2 guests (+tax/tip)
Private charter up to 6 guests $545 (+tax/tip)

Plus there is a 10% amusement tax in St. Michaels harbor, and a customary 20% tip for the crew.
Wine Cruises are available Sun-Sat 12:30-2:30pm and 3:00-5:00pm.
Sail Selina wine cruise is located in St Michels MD, just an hour from Annapolis, making it the perfect day trip to share with loved ones or make it a special girls night out.
Limited to just 6 guests for a truly personal experience.

Parking: Free parking where we are parked at the Harbour Inn, 101 N Harbor Road, St Michaels MD 21663. If there are no spaces available, then there is parking on the side streets and along the waterfront down past where the work boats tie up.

Beer: Sometimes there is someone in your group who would just rather drink beer. That’s OK too, just let us know and we will be happy to give them a beer tasting tour while you sip your wine.

St. Michaels Yacht Beer Tasting Cruise
2023-06-02 15:00 - 2023-10-29 17:00
Available per person or Private Charter
Join us for an unforgettable experience on our ice-cold Beer Tasting Cruises Be prepared for an unforgettable adventure on our beloved historic yacht Sail Selina II. Indulge in the aroma, taste, and quench your thirst with our cold, refreshing beers.
A 2-hour tour on our beautifully kept sailing boat offering a luxurious and comfortable sailing experience. Guests have consistently praised the impeccable condition of the sailboat, making it the perfect setting for a memorable trip on the water.

Person

Per person Starting at $90- $115

Private Charter

Private Charter starting at $675

Max 6 passengers: Must be 21 or older to participate in the beer tasting portion of this trip
Children: Kids of all ages are welcome aboard the Selina II. Example, mom, dad, and their six-month-old are three guests, not two.
Cancellation 24/72 hrs: Reservations made on a per person basis cancellation is 24 hrs. Private Charters are 72hrs.
Parking: Free parking where we are parked at the Harbour Inn, 101 N Harbor Road, St Michaels MD 21663. If there are no spaces available, then there is parking on the side streets and along the waterfront down past where the work boat tie up.

Wine: Wine is available for any guest who may prefer this.

WINE TASTING CRUISES

Tall Ship Kalmar Nyckel Sails in Cambridge (June 2nd)
2023-06-02 13:00 - 15:30

Cambridge Farmers’ Market
2023-06-01 15:00 - 2023-11-04 18:00
Operating May through November in 2023, Every Thursdays from 3pm – 6pm, the Long Wharf Farmer’s Market is a local favorite! What’s better than a waterfront Farmer’s Market?
The market is situated in the Long Wharf park, nearby public parking. The market is within walking distance to the Municipal Marina, Skipjack Nathan, the replica Choptank River Lighthouse and downtown Cambridge along historic brick-paved High Street.
Approximately 18 or more vendors can be found throughout the season, including many local Dorchester and Eastern Shore regional farmers, crafters, and specialty food vendors.

Crab Feast Cruise
2023-06-01 12:00 - 2023-08-31 15:00
Take a relaxing 3-hour cruise on one of the most exciting attractions offered on Maryland’s Eastern Shore!
The boat offers a fully enclosed lower deck with heating and air conditioning, as well as a covered upper deck with a great view of the river.
Catered by Suicide Bridge Restaurant and features local seafood and Eastern Shore favorites including Steamed Crabs, Crab Soup, Fried Chicken, Clam Strips, Fresh Local Corn, Coleslaw, Dessert and Non-Alcoholic Beverage

Sail on the Skipjack Nathan (May 27th)
2023-05-27 13:00 - 15:00

Classic Motor Museum Memorial Day Parade
2023-05-27 10:30
The CMM is proud to bring our community together in honoring the service of our military heroes by hosting the Annual Classic Motor Museum Parade. The participants will line up at Perry Cabin Park, and will head down Talbot St, pausing near Railroad Avenue for the emcee to announce the make, model, and driver of the vehicle, before continuing through the rest of town until turning left onto Seymour Avenue. The parade will end at the Classic Motor Museum at 102 E. Marengo St. where we invite the public to join the museum for refreshments and entertainment.

St. Michaels Farmer’s Market
2023-05-27 08:00 - 2023-11-18 12:00
The St. Michaels Farmers Market features farmers and vendors selling locally grown and caught vegetables, meats, and fish, plus handmade crafts and live music.The St. Michaels Farmers Market features farmers and vendors selling locally grown and caught vegetables, meats, and fish, plus handmade crafts and live music.

Karaoke Night – The Jetty Restaurant and Dock Bar (May 24th)
2023-05-24 18:30 - 22:00
Come out to the Jetty Restaurant and Dock bar for amazing food and the best drinks in the area! Enjoy the beautiful view and if you are feeling the vibes come rock the dock with Karaoke night.
Every Wednesday from 6:30 – 9:30 head to the Jetty restaurant and Dock Bar for Karaoke night.

39th Annual Oxford Fine Arts Fair
2023-05-20 10:00 - 16:00
On Saturday and Sunday, the prestigious juried exhibit draws a wide selection of regional collectors as well as from major cities along the Eastern Seaboard. The much-anticipated annual show is well known throughout the area and celebrated as the season’s “kick-off” for art lovers.
The exhibit featuring 36 artists from the mid-atlantic region and beyondis open to the public from 10 a.m. to 4 p.m. The raffle of beautiful artwork donated by the artists happens at the end of the show.

Lunch items are available onsite for purchase on both days. The famous strawberry shortcake is not to be missed.

St. Michaels Farmer’s Market (20th)
2023-05-20 08:00 - 12:00
The St. Michaels Farmers Market features farmers and vendors selling locally grown and caught vegetables, meats, and fish, plus handmade crafts and live music.

Cambridge Classic Powerboat Regatta
2023-05-20 - 2023-05-21
The oldest active powerboat race in the country happens right here in Dorchester County, Maryland. This year’s race will be held on May 20-21, 2023 on the Choptank River. About 70 boats are expected to be on hand to create an exciting two days of racing. Admission is FREE with a $5 a day charge for parking. Food and drinks will be available.
The races happen on Hambrooks Bay off the Choptank River in Cambridge, Maryland. Watch on land on bleachers at Gerry Boyle Park at Great Marsh. Spectators can also watch the Cambridge Classic from their own boats on the water. The fleet will raft at Rooster Point. A no-wake zone will be established from Howell Point to the Choptank River Bridge.
From 10am to 5pm both days (weather permitting), boats will be racing in these classes – Grand Prix Hydroplanes, H350 Hydroplanes, 2.5 Liter Hydroplanes, Formula 2500, and Jersey Speed Skiffs. The Hydroplane Racing League (HRL) will be kicking off their 2023 Season at this race and will be coordinating all race activity.

Kent Island Farmers’ Market (May 18th)
2023-05-18 15:30 - 18:30

Karaoke Night – The Jetty Restaurant and Dock Bar (May 17th)
2023-05-17 18:30 - 22:00

Old Courthouse Distillery
2023-05-17 15:00 - 2023-11-30 21:00
Once the oldest working courthouse in Maryland now currently the Old Courthouse Distilling was established in 2019!
Distillery Hours

Wednesday – 3:00pm to 9:00pm
Thursday – 3:00pm to 9:00pm
Friday – 3:00pm to 9:00pm
Saturday – 2:00pm to 9:00pm

Blanco Rum
This rum is twice distilled, then cut and charcoaled filter for a super smooth and sweet taste. Enjoy alone or in your favorite rum drink
Agave Sunrise
– Is our agave spirit also twice distilled, cut and charcoal filtered. The result is an ultra smooth and phenomenal tasting agave spirit.
Rye Whiskey
– While we are making bourbon now, and have barrels aging, the whiskey process takes several years of aging to perfect this delicious brown liquid. We are looking forward to releasing out whiskey, but until then, we’ve purchased several barrels from Indiana, for blending cutting and bottling right here in Centreville MD. This is a very sweet rye, with a hint of spice. It is bottled at 95% ABV.

Wine Tasting at St. Michaels Winery
2023-05-15 - 2023-10-31
Wine tastings Hours
Monday – Saturday (12pm-5pm)
Sunday (12pm-4pm)
With 18 wines in our cellar, we have something for every pallet.
Tasting Fee: $1.00 per wine sampled
Glasses: Glasses of wine are available each and every day. We also will have sangria or mulled wine occasionally, depending on the weather and our whims.
Bottles: After a wine tasting, be sure to grab a few bottles of your favorites. Take them with you, or leave them with us while you explore town.
​Group Tastings: Tastings for groups of 12 or less guests.

Emily’s Produce
2023-05-15 - 2023-11-19
The market with a U-Pick strawberry, blackberry, blueberry and cherry patch, U-Cut flower patch, and a beautiful selection of hanging baskets, perennials, annuals, and planters straight from their own greenhouse. Delicious homemade desserts are made daily.

The market offers the freshest and sweetest homegrown sweet corn and tomatoes starting in late June as well as a wide variety of other fruits and vegetables.
Shop for unique and great tasting jams, jellies, relishes, and sauces made with the freshest fruit and vegetables of the season. Emily’s also offers their own grass-fed beef and farm-fresh eggs.
Children are always welcome to enjoy Kyle’s Farm Fun a free play area for children. Plus, visit with the chickens, rabbits, and pygmy goats!

Hours of Operation

Wednesday: 9am – 4pm
Thursday: 9am – 6pm
Friday: 9am – 6pm
Saturday: 9am-5pm
Sunday: 9am-5pm
Monday: 9am – 6pm
Tuesday, closed

Blackwater Refuge Wildlife Drive
2023-05-15 - 2023-08-31
The 4-mile long Wildlife Drive is open from sunrise to sunset every day, takes you through several types of wildlife-rich habitat found at Blackwater National Wildlife Refuge.

Wildlife Drive is paved, and can be accessed by vehicle, bicycle, or foot. An entrance fee is required for the Drive, and can be paid at the self-service kiosk at the head of the Drive. The daily fee for the Wildlife Drive is $3 per vehicle and $1 per hiker or biker.

Easton Farmers Market (May 13th)
2023-05-13 08:00 - 13:00

Cambridge Farmers' Market
2023-05-11 15:00 - 18:00
Operating May through November in 2023, Thursdays from 3pm – 6pm, the Long Wharf Farmer’s Market is a local favorite! What’s better than a waterfront Farmer’s Market? The market is situated in the Long Wharf park, nearby public parking. The market is within walking distance to the Municipal Marina, Skipjack Nathan, the replica Choptank River Lighthouse and downtown Cambridge along historic brick-paved High Street.
Approximately 18 or more vendors can be found throughout the season, including many local Dorchester and Eastern Shore regional farmers, crafters, and specialty food vendors.
