September Events Bay to Beach

Summer gives way to glorious September here on Delmarva. The locals’ best kept secret is the beauty of the beginning of fall bay to beach. Music festivals, art shows — so much is happening throughout this month. It’s one of the best times of year to explore our small towns. Here’s a round up of what’s happening to help you plan a September getaway!

National Folk Festival
September 6-8, 2019, Salisbury, MD

An exuberant traveling festival that celebrates the diverse cultural expressions of 21st-century Americans, the National Folk Festival is produced by the National Council for the Traditional Arts (NCTA) in partnership with communities around the country. In 2019, the National will celebrate its 79th year in Salisbury, Maryland. Musicians and craftspeople from every state and most U.S. territories have participated in this “moveable feast of deeply traditional folk arts.” Presented to audiences free of charge over three days, National Folk Festivals have drawn audiences of 100,000 to 175,000 annually since 1987. For more information, visit

Arts Alive at Five! in Downtown Dover
Friday, September 6th, 5-9 p.m.

Community-based and regional artists (musical, visual, culinary) provide demonstrations/workshops inside 15 shops and outdoors (weather-permitting) on the first Friday of every month in downtown Dover, all free and open to the public. For more information, visit

Dover First Fridays

First Friday Opening Reception
September 6th, 5-7pm, Ocean City Center for the Arts

Six new art exhibitions including a juried show by members of the Maryland Federation of Art fill the galleries of the Ocean City Center for the Arts during September. 

The public is invited to the free opening reception at the Arts Center on 94th St. bayside on First Friday, Sept. 6, from 5 to 7 p.m. to meet the artists and enjoy complimentary hors d’oeuvres. The shows will run until Sept. 28. For more information, visit

Berlin Small Town Throw Down
September 7th, 1pm-6pm, Berlin, MD

Berlin Honky Tonk Country Music Festival featuring Ruthie and the Wranglers, Boy in Black – Johnny Cash Tribute Band, and Jason Morton & the Chesapeake Sons. Burley Oak Brewing Company will be on hand with their beer truck and all beer sales benefit our Berlin MD Arts & Entertainment Committee. Food on the street and our restaurants will offer sit down dining service! Dancing in the streets is encouraged or just bring a chair and enjoy! Sponsored by The Atlantic Hotel.

Bethany Beach Boardwalk Arts Festival
Saturday, September 7th, 10:00am to 5:00pm

This annual event hosts over 100 juried artists to showcase and sell their work. The featured artists bring unique creations representing a variety of different mediums including paintings, photography, woodwork, metalwork, clay, baskets, and jewelry. For more information, visit

Boardwalk Arts Festival
Bethany Beach Boardwalk Arts Festival

Second Friday Art Stroll & Makers Market
Friday, September 13th, 5pm, Berlin, MD

Stroll downtown Berlin to view local art inside shops and restaurants and outside on Jefferson Street. Most of the shops are open late! Event by Berlin Arts and Entertainment.

Second Saturday Open Air Market at the Artsway
Saturday, September 14th, 10am – 3pm,

The Denton Artsway, Fourth Street, Denton
The Second Saturday Open Air Market features vendors, fresh produce, music, and fun for the whole family! There will also be a community yard sale benefitting the Caroline County Council of Arts and the Fiber Arts Center of the Eastern Shore (FACES) from 10am – 3pm. FREE!
[email protected]

The 3rd Annual Multicultural Festival 
Saturday, September 14th, 11am-3pm
North County Branch Library, Greensboro, MD

Enjoy West African and Salsa Dance demonstrations, 
Communal Drumming, and more! Taste diverse foods – Indian and Mediterranean, Mexican and Caribbean.There will be plenty of activities for kids including face painting, a moon bounce, double dutch and various games played around the world. Meet and greet internet personality and entertainer Yvng Swag, also seen on MTV’s Wild N’ Out. Sponsored by the Friends of the Library!

Chestertown Jazz Festival
Saturday, September 14, 11am – 6pm, Wilmer Park, Chestertown, MD

The Chestertown Jazz Festival offers a day of gorgeous music overlooking the Chester River, with featured vocalist Alicia Olatuja, violinist/pianist/composer Gregor Huebner with El Violin Latino, the Greg Thompkins Quintet and more.  Tickets $25 in advance, $35 at the gate, $15 students.  Food, beer and wine available for purchase.

 Alicia Olatja
 Alicia Olatja 

Paint Berlin Plein Air
September 18th – 21st , 10am-5pm, Berlin

Participating artists from across the region will grace Berlin’s streets, sidewalks, marshes, and green spaces from September 18 – 21 in this annual Paint Berlin, plein air competition. Artists will paint outdoors in location of their choice providing our Community and visitors with the unique experience of seeing the surroundings through their eyes while preserving the best aspects of our town and county. Visitors are invited to come and watch artists work during this event and attend the free and open to the public “Wet Paint” sale and exhibit to be held on Saturday, September 21, from 11 am to 3 pm, featuring artwork created during this event. Artwork on the exhibit will be judged and awards will be presented at noon. Event by the Worcester County Arts Council. 

Sand Castle Home Tour
September 19th & 20th, 9:30am – 4pm

Have you gotten your tickets to the Sand Castle Home Tour yet? This year’s tour includes 10 resort homes sure to please everyone’s tastes – and inspire decorating schemes, architecture, and outdoor lifestyles. The homes range from impressive large waterfront residences to quaint cottages located in Ocean City, West Ocean City, and Ocean Pines. Start out at the Arts Center on 94th St. where you will pick up your tour booklet, goody bag, and blue booties. Then you can tour the homes at your own pace over two beautiful days. Sponsored by the Art League of Ocean City.

Watercolor of House in home tour
Sand Castle Home Tour

Fiddlers Convention
September 20th – 22nd  in Berlin, MD

Friday, Sept 20th – 7pm-10pm – Concert featuring “Jakob’s Ferry Stragglers” and “Robert Mabe’s Irish Banjo” Saturday, Sept 21st – 10am-5pm – Fiddler’s Convention Competition followed by the event headliners in the afternoon. Free Parking Shuttle Service Available from Berlin Intermediate School (309 Franklin Ave). Sunday, Sept 22nd – 12noon-3pm  – Gospel Bluegrass Jam w/ Stevenson’s Crossroads and Blue Crab Crossing at the Taylor House Museum. For more information, visit the Berlin Chamber of Commerce,

2nd Annual Milford Ladybug Music Festival
September 21st

Over 40 artists will perform this year from as far as Canada, Connecticut, and Nashville to entertain music lovers.  The 2019 Headliner is Willow Hill, a husband and wife country pop act from Nashville.  Willow Hill spent a decade building a dedicated following in the region with their former band Lovebettie. Willow Hill performs from  8:00-9:00pm on the main stage.  Rachael Sage, a New York City based singer/songwriter, producer, and owner of MPress Records, will headline the Library Amphitheater stage. Sage has received acclaim from the New York Times, Wall Street Journal, Rolling Stone Magazine, and Billboard Magazine, and has shared the stage with Ani DiFranco, Sarah McLaughlin, Shawn Colvin, and more.  Other notable performers this year include Hoochi Coochi, Nalani & Sarina, and Christine Havrilla.  For a full list of all artists performing with links and more information, please visit

Lady Bug Festival Headliners
Milford Ladybug Music Festival

GrooveFEST: Downtown Music Festival 
Saturday, September 21st, Cedar & Race Streets, Cambridge, MD, 5pm – 10pm

This annual downtown music festival returns with BLUES, Soul, Jazz, Funk and more! This fun and funky street festival takes place on Race Street in downtown Cambridge, highlighting the city’s rich musical roots and talent.

2019 Performances by Hoppie Vaughan and the Ministers of Soul, SoulTET, UPHILL Swampland Blues and more! Event hosts brews, BBQ and vendors!

Downtown GrooveFEST in Cambridge

Crisfield 4th Saturday Bay Strolls celebrates National Good Neighbor Day and Taste of Crisfield
September 28th, 4-7pm

Crisfield 4th Saturday Bay Strolls celebrates National Good Neighbor Day September 28th from 4 to 7 pm at the City Dock. This annual holiday was first proclaimed by President Jimmy Carter in 1978.  This day is aimed at raising public awareness that good neighbors help achieve human understanding and build strong, thriving communities. Whether you live in Crisfield or on the Shore or are just visiting, have a good neighbor and meet a good neighbor at this event celebrated with live music, artists and vendors, beer and wine and festival foods.

The Taste of Crisfield is a free event takes place 11 am to 4 pm at Somers Cove Marina, 715 Broadway Avenue and is a waterfront festival celebrating the history, fishing culture and cuisine of the Chesapeake.  Highlights include in-great local food, demonstrations, children’s activities, and entertainment.  All kinds of seafood will be available including crab cakes, oysters, soft shell sandwiches and steamed Crabs. Are you good with your fishing rod? Prove it by winning the 1st Annual Casting Contest! For more information check out

Crisfield Good Neighbors
Crisfield Neighbors
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