Eastern Shore Vacation Rentals

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

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
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

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
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.

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
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.

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.

2023 Spring Fling
2023-04-22 18:00 - 23:00
Let’s welcome all new beginnings for Cambridge Main Street with an evening of dinner, drinks, dancing, and a live auction. Ticket price includes 2 drink tickets. We look forward to welcoming you!
Funds raised from Spring Fling go to support Cambridge Main Street operating expenses.

Family Art Day – eARTh Arts Day Extravaganza!
2023-04-22 10:00 - 13:00
Make art together during these fun days for all ages!
eARTh Arts Day Extravaganza!
Saturday, April 22
10 am–1 pm
FREE
There is no cost to participate in Family Art Days, but please let AAM know if you are coming, as it will help them plan. Sign up online!

Taste of St. Michaels Tasting Crawl
2023-04-15 11:00 - 16:00
Taste of St. Michaels includes a Tasting Crawl on Saturday, April 15th from 11am – 4pm which allows participants to literally eat their way around the Town at award-winning restaurants. Each tasting venue will have tasting selections that feature food and drinks, Chesapeake Bay inspired. Tastings can be purchased, ranging from $1-$5, at participating venues around town so as to enjoy their decadent treats. As you stroll about Town, check out the restaurant specials available all weekend. Event is rain-or shine. Sponsored by the St. Michaels Business Association.

Easton's Annual Easter Egg Hunt
2023-04-08 10:00 - 12:00
Thousands of eggs will be spread out on the Talbot County Courthouse grounds on Saturday, April 8. Enjoy free face painting and an appearance by the Easter Bunny!

Saint Patrick's Day Parade
2023-03-17 17:30 - 19:00
Each year Easton celebrates Irish heritage during our St. Patrick’s Day festivities!
The Easton Saint Patrick’s Day Parade starts at 5:30 p.m. and features over 40 floats, bands, classic cars, and local businesses. The Annual Potato Races take place downtown immediately following the parade. Come celebrate with us on Saint Patrick’s Day.
