Eastern Shore 9/19 Picks

One of the world's most grueling tests of physical and mental endurance takes place right here in Dorchester County, Maryland. Dorchester is one of the few communities to host two IRONMAN events. IRONMAN Maryland is a full-length triathlon: The day begins at sunrise with a 2.4-mile open water swim in the Choptank River, then a 112-mile bike ride through scenic Blackwater National Wildlife Refuge and surrounding areas on one of the best bike courses in North America as voted on by athletes. The third and final leg is a full marathon – 26.2 miles, including time running through downtown Cambridge buoyed by the cheers of thousands of supporters. The transitions happen at Gerry Boyle Park at Great Marsh in Cambridge, Maryland and is the best spot for spectators throughout most of the race. Then the action moves to the finish line at Long Wharf Park in Cambridge, where triathletes cross the finish line up until midnight. Find out more about the race. The race is known for its great show of community support, and needs 1,000 volunteers to make it happen. Meet other volunteers and athletes by signing up for volunteer tasks before, during, and after the race. Register to volunteer here.

POW MIA Memorial Car Show, will be hosted by the Sons of the American Legion Squadron 159 Chincoteague, VA on September 19 at the Chincoteague Carnival Grounds, 3648 Main Street, from 9am - 2pm. Registration is $15/vehicle. Top 25 & Best in Show trophies. First 50 receive a dash plaque. 4 motorcycle trophies sponsored by American Legion Riders 159 Free for the public to attend. We hope you will join us for a great day supporting veterans and remembering those who have yet to come home. CALL FOR VENDORS: Do you have a food truck, unique art or craft, do direct sales, or just want to promote your business or organization? The POW MIA Memorial Car Show is looking for vendors to join us on September 19 from 9am - 2pm at the Chincoteague Carnival Grounds. Not only will you get to enjoy the

The 34th Annual Native American Festival hosted by the Nause-Waiwash Band of Indians is scheduled for September 19, 2026, at the ball field under the water tower at 214 Middle St, Vienna, MD. It features traditional drumming, dancing, educational exhibits, Native arts and crafts vendors, and Indigenous foods. Gates open at 10am, and Grand Entry will be at 12pm. Admission is $10 per person. Children 4 and under are free. For groups of 10 or more, call ahead at 443-521-0753. Rain or shine. Seating is limited, so please bring your own lawn chairs or blankets. Questions? Email nausewaiwash@gmail.com.

Join us for the Ballet on the Beach Dance Festival on Assateague Island! Cosponsored by Assateague State Park, this free professional performance take...

Find Us Contact Home Search Search Menu X Z Accommodations Hotels Motels Bed & Breakfasts Weekly Rental Agencies Weekly Rentals by Owner Accommodations by Type All Accommodations X Z Restaurants & Food Breakfast Lunch Carry Out Catering Fine Dining Waterfront Dining Restaurants by Cuisine All Restaurants & Food X Z Events & Activities Movie Times Calendar of Events Beaches and Parks Golf Courses Rehoboth Golf Directory Kid Stuff Family Fun Rainy Day Fun All Activities X Z Nightlife Nightlife Music Schedules Movie Times X Z Shop Apparel The Outlets Complete Shop Directory X Z Business Directory Featured Businesses Pay/Purchase Advertising Pay/Purchase Advertising Business Directory X Z Real Estate Main Real Estate Looking to Buy? Trying to Sell? Sales Agencies Weekly Rental Agencies Vacation/Year-Round Rentals Commercial Real Estate Building/Home Improvement Other Helpful Links X Z Community Our Community Visitor's Services & Parking Local News & Traffic Local Weather Transportation Beach Weddings Rehoboth Beach FAQ to Rehoboth Jobs Town History My Rehoboth Advertise With Us Pay/Purchase Advertising Saturday, September 19 - Saturday, September 19 Delaware Seafood Festival 11am-5pm. The Delaware Seafood Festival will be held at Schellville in Rehoboth Beach. In addition to providing a day of local flavor and family fun, the event also serves as a fundraiser for two area nonprofits, the Delaware Center for the Inland Bays and the Delaware Restaurant Foundation.The festival will also include raffle baskets and a Boat of Booze raffle, an actual boat filled with liquor and swag. Tickets for the Delaware Seafood Festival are available at delawareseafoodfestival.com . Search Rehoboth.com Search Search

Find Us Contact Home Search Search Menu X Z Accommodations Hotels Motels Bed & Breakfasts Weekly Rental Agencies Weekly Rentals by Owner Accommodations by Type All Accommodations X Z Restaurants & Food Breakfast Lunch Carry Out Catering Fine Dining Waterfront Dining Restaurants by Cuisine All Restaurants & Food X Z Events & Activities Movie Times Calendar of Events Beaches and Parks Golf Courses Rehoboth Golf Directory Kid Stuff Family Fun Rainy Day Fun All Activities X Z Nightlife Nightlife Music Schedules Movie Times X Z Shop Apparel The Outlets Complete Shop Directory X Z Business Directory Featured Businesses Pay/Purchase Advertising Pay/Purchase Advertising Business Directory X Z Real Estate Main Real Estate Looking to Buy? Trying to Sell? Sales Agencies Weekly Rental Agencies Vacation/Year-Round Rentals Commercial Real Estate Building/Home Improvement Other Helpful Links X Z Community Our Community Visitor's Services & Parking Local News & Traffic Local Weather Transportation Beach Weddings Rehoboth Beach FAQ to Rehoboth Jobs Town History My Rehoboth Advertise With Us Pay/Purchase Advertising Saturday, September 19 - Saturday, September 19 Indian River Marina Autumn Art Festival 10am-5pm, Indian River Marina, 39415 Inlet RD (south of Dewey Beach), Delaware Seashore Park. Free admission. Food trucks, music, wine and craft beer tastings, artisans and crafters, pumpkin fun for the entire family. It's the perfect way to support small businesses and find unique gifts for any occasion. Mark your calendars and bring your loved ones—it's going to be a blast! See you there! https://destateparks.com/Programs Search Rehoboth.com Search Search

The St. Michaels Restaurant Association will host its inaugural Community Harvest Supper, with Inn at Perry Cabin serving as the setting for this special community gathering. This family-style Sunday supper brings together local chefs, farmers, restaurants, and neighbors for an evening centered around good food, live music, and community. Proceeds from the event will support the Community Garden, Community Center, and Farmers Market, the institutions that help make St. Michaels such a special place to live, work, and gather. Participating restaurants: Ava's Pizzeria & Wine Bar Bistro St. Michaels Foxy's Harbor Grille Lyon Rum Olivins Tasting Room Royal Oak Catering Ruse Restaurant STARS Restaurant Tilghman Island Baking Wylder Hotel Tilghman Island Participating farms: Bay Mushrooms…

Find Us Contact Home Search Search Menu X Z Accommodations Hotels Motels Bed & Breakfasts Weekly Rental Agencies Weekly Rentals by Owner Accommodations by Type All Accommodations X Z Restaurants & Food Breakfast Lunch Carry Out Catering Fine Dining Waterfront Dining Restaurants by Cuisine All Restaurants & Food X Z Events & Activities Movie Times Calendar of Events Beaches and Parks Golf Courses Rehoboth Golf Directory Kid Stuff Family Fun Rainy Day Fun All Activities X Z Nightlife Nightlife Music Schedules Movie Times X Z Shop Apparel The Outlets Complete Shop Directory X Z Business Directory Featured Businesses Pay/Purchase Advertising Pay/Purchase Advertising Business Directory X Z Real Estate Main Real Estate Looking to Buy? Trying to Sell? Sales Agencies Weekly Rental Agencies Vacation/Year-Round Rentals Commercial Real Estate Building/Home Improvement Other Helpful Links X Z Community Our Community Visitor's Services & Parking Local News & Traffic Local Weather Transportation Beach Weddings Rehoboth Beach FAQ to Rehoboth Jobs Town History My Rehoboth Advertise With Us Pay/Purchase Advertising Sunday, September 20 - Saturday, September 26 Inaugural Downtown Rehoboth Beach Cocktail Week Rehoboth Beach Main Street and Dogfish Head are shaking things up this fall with the inaugural Downtown Rehoboth Beach Cocktail Week. With bars and restaurants around town slated to join in the fun, the celebration of creativity, flavor and local mixology talent will run from Sunday, Sept. 20 to Saturday, Sept. 26. All week long, guests can stop by participating locations to enjoy exclusive cocktail specials crafted with Dogfish Head Distilling Co. spirits. As part of Dogfish Head’s Beer & Benevolence philanthropy program, $1 from each featured cocktail sold at a participating location will be matched and donated to Rehoboth Beach Main Street. Participating restaurants and bars include: Above the Dunes, Dogfish Head Brewings & Eats, Dogfish Head Chesapeake & Maine, Downtown Blues, Drift Seafood & Raw Bar, Kiwi's Kove, Purple Parrot Grill, Shorebreak Lodge, Sirocco Food & Drink, Somewhere, The Pines Coastal Tavern and Victoria’s Restauarant. Rehoboth Beach Main Street is a not-for-profit, volunteerdriven organization with the mission to foster and promote a vibrant, year-round, in-town experience for businesses, residents and visitors alike. https://www.downtownrb.com/ Search Rehoboth.com Search Search