Annual Events on the Eastern Shore

Spring Events | Fall Events | Free Events | July 4 Events | Holiday Events

  Spring Events

Spring on the Eastern Shore is a celebration of the area awakening--boats being launched, sparkling blue water and everything in full bloom.  Plan a weekend getaway to dust off those cobwebs from a long, cold winter and engage in one of the many athletic events or simply go it alone and rent bikes or kayaks for a more leisurely pace.  You may also consider partaking in one of our wine or food festivals, or some of the small town celebrations.  Easter weekend is also popular, so be sure to reserve early!

TALBOT RESTAURANT WEEK
April 2-8, 2017
Participating restaurants offer prix fix lunches and dinners, many with special menus designed to
showcase their finest dishes.

WINEFEST AT ST. MICHAELS
April 29-30, 2017
WineFest is Maryland’s premiere wine event, featuring hundreds of highly-rated international, U.S. and Maryland wines at tasting venues located throughout the town of St. Michaels.

OXFORD DAY
April 22, 2017
Events include a parade, live music, ferry rides, and a dog show. There will also be activities for kids and lots of food!

ST. MICHAEL’S RUNNING FESTIVAL
May 20, 2017
The St. Michaels Running Festival is one of the premier destination races in the Mid-Atlantic.  Based in one of the oldest waterfront towns on the Chesapeake, runners will be treated to gorgeous water views, a quick mile past charming main street shops for the half marathon and after-party in downtown St. Michaels.

CHESAPEAKE TOUR DE CURE
May 21, 2017
The Tour de Cure is more than just a cycling event, it’s a day packed with excitement and energy where riders of all levels join forces in the fight to Stop Diabetes® and raise critical funds for diabetes research, education and advocacy in support of the American Diabetes Association.
 
IRONMAN 70.3 EAGLEMAN TRIATHLON
June 11, 2017
Triathletes swim 1.2 miles in the waters of the Choptank, cycle 56 miles through the stunning Blackwater National Wildlife Refuge, and run 13.1 miles through the streets of the town—70.3 miles in all.

 
Summer Events

Ahhhhh, Summer!  The season we wait for all year!  Summer itself is an event, with endless activities at the ready to enjoy--swimming, boating, crabbing and fishing, kayaking and paddleboarding, or exploring our quaint towns. Vacationing has never been so relaxing when all you have to do is step outside to take in the Bay breezes or relax by the pool.  July 4 week is extra special, with waterfront fireworks in several towns, an old fashioned carnival in Easton, and many small town events and celebrations.  

PLEIN AIR EASTON ART FESTIVAL AND COMPETITION
July 17-23, 2017
Plein Air Easton is the largest and most prestigious juried plein air painting competition in the United States. Artists from all over the US and beyond apply to this competition and those who are selected paint throughout Talbot County during the Festival week. The resulting original works of art are on then on display, awards are given, and the paintings are sold. Highlights include the Festival’s Quick Draw Competition and demonstrations, workshops, exhibits and lectures for all ages.

July 4 Celebrations

No one does Independence day like the Eastern Shore!  With several fireworks displays throughout the area--many of them waterfront--carnivals and big band celebrations, there are plenty of ways to celebrate the Red, White and Blue
for all ages.

ST. MICHAELS
Saturday, July 1, 2017 (Chesapeake Bay Maritime Museum)


Enjoy an evening of music, food and waterfront fireworks beginning at dusk.  Bring blankets to sit along the beautiful campus of CBMM and enjoy the show!  For more information, click here.

OXFORD
Monday, July 3, 2017 (Tred Avon Yacht Club) . Small town charm mixes with a fireworks display that will not disappoint.  Plan on grabbing dinner at one of the local crab houses prior to and strolling to the yacht club for the show.  For more information, click here.

EASTON
Tuesday, July 4, 2017 (located at Marlboro Avenue and St. Michaels Road, behind Target)The old fashioned Easton Carnival wraps up with an Independence Day extravaganza of music and fun, with fireworks at dusk.  This is the area's main show, and it never disappoints!  For more information, click here.


 CAMBRIDGE
 Tuesday, July 4 (Choptank River)  
 Watch a Fourth of July fireworks show over the Choptank River.  Show begins at dusk. Best  viewing spots include Great Marsh Park, near Somerset Avenue  and Hambrooks Boulevard; and  Long Wharf Park, near High and Water Streets. Bring your own  lawn chairs or blankets and  snacks. For more information, click here




ROCK HALL
Monday, July 3 (Rock Hall Harbor)  Some of the best fireworks on the Chesapeake Bay!


CHESTERTOWN
Tuesday, July 4, 2017 (fireworks over the Chester River, good viewing from Wilmer Park)

 FALL EVENTS

IRONMAN MARYLAND 2017
October 7, 2017
Watch the excitement as 2,000 triathletes from all over the world take on a 140.6 mile triathlon in and around Cambridge, MD—one of only a dozen IRONMAN full-length triathlons in the country.
 
TILGHMAN ISLAND DAY
October 22, 2017
Live music, fresh seafood, boat docking contest and races. Fun for the family!

FALL INTO ST. MICHAELS
October 21-23, 2017
Enjoy the beauty of the foliage color change in historic St. Michaels, Maryland. The change of the season brings excitement and vibrant color to the town, as residents and businesses celebrate Fall into St. Michaels. Visitors love the cool breezes, gorgeous sunsets and the perfect setting for a walk or bicycle ride. www.smba.org

CHESAPEAKE FILM FESTIVAL
October 27-29, 2017
With all of today’s movie viewing options, the film festival is still the only place to see great new works, discover hidden treasures, and engage with the heart of an artist.

DOWNRIGGING WEEKEND
October 27-29, 2017
Now in its 17th year, Sultana’s Downrigging Weekend Tall Ship and Wooden Boat Festival has evolved into one of the largest annual Tall Ship gatherings on the East Coast. Visitors to festival can expect to see a waterfront packed with ships, schooners, and wooden boats; performances by world-class musicians; lectures by nationally recognized authors and filmmakers; plenty of opportunities to go sailing as part of a fleet of “Tall Ships”; and the chance to spend the weekend in Chestertown – one of America’s best preserved historic seaports. Don’t miss it!

OYSTERFEST
October 28, 2017
Celebrate everyone's favorite bi-valve with live music, retriever demonstrations, and oyster many ways, of course!

WATERFOWL FESTIVAL
November 11-13, 2017
This wildlife art show, sportsman’s expo and small-town festival celebrates all things “Eastern Shore” and showcases Easton in its autumn glory.
*Reserve early, properties for this event book quickly.

   Holiday Season

THANKSGIVING ON THE SHORE
November 24-27, 2017
Whether looking for a large family home to gather loved ones, or a cottage for a quick getaway and quiet weekend, our properties are available for the Thanksgiving holiday.
*Reserve early, properties for this event book quickly.

CHRISTMAS IN ST. MICHAELS
December 9-11, 2017
Find out why St. Michaels is consistently named as one of the country's best Christmas destinations!  

NEW YEAR'S EVE
December 31, 2017
Looking to set a quiet tone for the new year?  The Eastern Shore is the perfect place to usher in 2017.
*Reserve early, properties for this event book quickly.

 
 FREE EVENTS
 
FIRST FRIDAY GALLERY WALKS
Head into downtown Easton the first Friday of every month to view incredible work by local artists and enjoy light refreshments.
 
ART WALK
Enjoy an evening in downtown Cambridge strolling by the art galleries, browsing a range of artwork, and enjoying free refreshments during the Art Walk, which happens the second Saturday of every month.
 

  FARMERS MARKETS

EASTON
The Farmers' Market is held every Saturday until December. Over 20+ vendors offering a variety of fresh fruits, organic vegetables, bison meat & products, sauces, baked goods, flowers, plants and craft items.

ST. MICHAELS
The market is a Saturday destination for locals, weekenders and boaters. Farmers offer fresh fruits and vegetables, meats, cut flowers, potted plants, breads and pastries, cow's milk cheeses, orchids, eggs and honey. It runs mid-spring through early autumn.