Get ready for an unforgettable day of music, shopping, and fun at the Classic Rock Music Fest at Somers Cove Marina!

Set against the stunning waterfront backdrop, this event features incredible live performances, delicious food, and a variety of local vendors offering unique finds.

Be sure to grab your tickets to see the Amish Outlaws, who will be taking the stage from 5–7 PM for an energetic and entertaining show you won’t want to miss.

Enjoy the electric atmosphere, scenic marina views, and a celebration of classic rock like no other. Come for the music, stay for the experience!

The Olde‑Tyme Peach Festival in Middletown, Delaware, is a beloved summer tradition hosted by the Middletown Historical Society.

First launched in 1993, the festival celebrates the town’s rich peach‑growing heritage—by the 1850s Middletown had become the heart of Delaware’s peach industry, shipping fruit to markets in Philadelphia, Boston, and New York.

Held annually around mid‑August, the festival kicks off at 8:45 AM with a lively peach parade down Broad Street—a festive start to a day crowded with over 27,000 attendees roaming Main Street (vehicle traffic closes for the event)

Throughout the day—from morning until 4 PM—visitors enjoy live music, a peach pie contest, a peach-themed car show, crafts, games, historical exhibits, artist showcases, local food vendors, and—as you'd expect—plenty of peaches to sample and buy

Altogether, the Olde‑Tyme Peach Festival delivers a vivid, family‑friendly celebration of Middletown's community spirit and agricultural legacy, honoring the fruit that helped shape the town’s identity.

Get ready for an unforgettable tropical celebration at the Aloha Luau!

From 3pm to 6:30pm, explore the vibrant Tiki Market, enjoy delicious eats from local food trucks, and let the little ones have a blast in the free Ohana Kid's Zone. Soak in the island vibes with live music from a Hawaiian Calypso Band and more exciting surprises throughout the afternoon.

Then, at 6:30pm, the evening heats up with a ticketed full-scale Luau experience you won’t want to miss—running until 8pm!

Don’t miss this fun-filled day of aloha spirit for the whole family!

Get ready for a full day of fall fun at the Apple Cider Sip & Shop at Fifer Farms! This family-friendly event features a lively vendor market filled with unique local goods and seasonal treasures—perfect for early holiday shopping or treating yourself.

Enjoy the sounds of live music as you sip on fresh apple cider and explore everything the farm has to offer. Kids will love the petting zoo and horseback rides, while everyone can join in on the u-pick apple adventures and other hands-on farm activities.

Be sure to visit the farm store for homemade jams, baked goods, and fresh produce, then satisfy your appetite at the farm kitchen with a delicious lunch and a scoop (or two!) of their famous farm-churned ice cream.

It’s a harvest celebration you won’t want to miss!

Get ready to embrace the flavors of fall at the 3rd Annual Apple Cider Festival at the Lewes Fire Department Station #2, located on Janice Road.

This family-friendly event celebrates all things apple and offers a delightful day out for attendees of all ages.

Savor the season with freshly pressed apple cider and indulge in delectable apple cider donuts.

The festival will feature over 50 local vendors and crafters, providing a fantastic shopping experience.

Children will enjoy the petting zoo, and everyone can explore the fire trucks on display.

Don't miss the opportunity to support the local fire department auxiliary while enjoying the festivities.

Mark your calendars and join the community in welcoming the autumn season with this charming celebration!

The Sweater Weather Get-Together is being held this October at the AMVets Post #2 in Millsboro, DE, bringing with it the cozy charm of fall and a festive atmosphere perfect for sweater season.

Along with light refreshments, warm drinks, and great company, guests can enjoy shopping a curated selection of local vendors offering handmade crafts, fall décor, boutique apparel, artisan candles, seasonal treats, and unique gift items.

Whether you're picking up something special for yourself or getting a head start on holiday shopping, the vendor market adds a fun and festive twist to this laid-back community event. It’s the perfect way to celebrate autumn—wrapped in your favorite sweater and surrounded by small-town charm.

Saddle up for a day of fun at the Sandy Boots Hoedown, where country charm meets family-friendly excitement!

Dust off your boots and hit the dance floor for some lively line dancing, or sit back and enjoy the twang of live Bluegrass music filling the air.

Brave souls can take a ride on the mechanical bull, while shoppers explore the rustic Mercantile Vendor Market filled with handmade goods, western wares, and unique finds.

When hunger hits, head over to the Watering Hole for ice-cold drinks and dig into mouthwatering BBQ vittles and classic fixins.

Kids will love the Kid’s Corral with fun activities just for them, and the whole family can enjoy scenic hayrides, themed photo ops, and surprises around every corner.

The Sandy Boots Hoedown promises an unforgettable day of music, laughter, and country-style celebration for all ages!

Mark your calendar for the Fall Vendor Market Village at the Seaside Tanger Outlets in Rehoboth Beach on Saturday, October 18, 2025, from 11 a.m. to 5 p.m.

This festive parking-lot pop-up, nestled in front of Mission BBQ, will host over 60 local small businesses showcasing beautifully crafted fall and holiday goods

Expect everything from boutique jewelry, seasonal décor, and artisan candles to boutique clothing, homemade treats, and unique gifts—perfect for seasonal browsing or early holiday shopping.

Held outdoors in the vibrant Tanger Outlets setting and paired with tax-free shopping from the main outlet stores, this event delivers a lively, community-driven atmosphere infused with autumn charm.

Don’t miss this opportunity to support local artisans while enjoying a crisp October day by the shore!

Get ready for a day of festive fall fun at the Fall Spooktacular hosted by Kirby & Holloway Provision Co. in Harrington, DE on Saturday, October 25, 2025, starting at 10 a.m.

This exciting event will feature over 70 local vendors offering seasonal crafts, handmade goods, boutique finds, and early holiday gifts.

Families can enjoy a wide variety of attractions, including trick-or-treating for kids, inflatable bounce houses, a petting zoo, and the delicious flavors of fall with fresh apple cider donuts.

Plus, don’t miss the chance to grab a bite from the Kirby & Holloway kitchen, serving up their famous breakfast and lunch favorites.

It’s a full day of shopping, snacking, and spooktacular fun for all ages!

Kick off the holiday season in style at the Holiday Market Kick-off at Tanger Outlets Seaside in Rehoboth Beach.

This festive outdoor event, located in the front plaza of the Seaside center, will feature a vibrant vendor market filled with handcrafted gifts, artisan goods, holiday décor, and seasonal treats perfect for early shoppers.

Enjoy the cheerful sights and sounds of the season as you browse unique finds from local makers, sip warm beverages, and soak up the holiday spirit.

Whether you're starting your gift list or just looking for a fun way to celebrate the season, this kickoff market sets the perfect tone for a joyful holiday shopping experience at the beach.

Get into the festive spirit at the Holiday Shoppes Craft & Vendor Show, held in November at the Delaware State Fairgrounds in Harrington.

This beloved annual event transforms the fairgrounds into a winter wonderland of shopping, featuring over 100 local artisans, crafters, and small businesses.

From handmade holiday décor and one-of-a-kind gifts to cozy candles, jewelry, gourmet treats, and personalized keepsakes, there’s something for everyone on your list—whether you’re shopping early or just soaking up the magic of the season.

In addition to the unique vendor market, visitors can enjoy food trucks and seasonal snacks, perfect for refueling between booths.

The indoor setting means you can browse comfortably, no matter the weather, and the festive music and friendly vendors make it a warm and welcoming experience for families, couples, and friends alike.

Whether you're a holiday décor enthusiast or simply love supporting small businesses, the Holiday Shoppes at the Delaware State Fairgrounds is the perfect place to start the season—and fill your sleigh—with style.

The Delcastle Technical High School Holiday Craft Fair, happening on November 15th, 2025, is a must-visit event to kick off the holiday season.

This annual celebration transforms the school into a winter shopping wonderland, featuring a wide array of vendors, crafters, and artisans showcasing their unique, handmade creations.

From the gymnasium to the cafeteria and all throughout the hallways, every inch of the school will be filled with festive booths offering everything from holiday decorations and home goods to jewelry, art, baked treats, and one-of-a-kind gift items.

Whether you're looking for something special for a loved one or just want to soak up the holiday atmosphere, this craft fair offers something for everyone.

It's a fantastic way to support local talent, enjoy a day of community cheer, and make serious progress on your Christmas shopping list.

Bring your family, your friends, and your holiday spirit—you won’t want to miss it!

Get a jumpstart on your holiday shopping at the Nobles Pond Vendor & Craft Fair, happening Saturday, November 16th!

This festive, one-day event is the perfect opportunity to find unique, handcrafted gifts for everyone on your list while supporting local artisans and small businesses.

Held indoors at ‘The Point,’ in the beautiful and spacious community center of the Nobles Pond development, the fair features over 40 vendors and crafters showcasing everything from handmade jewelry, home décor, and seasonal crafts to specialty foods, wellness products, and more.

The large ballroom offers a cozy yet vibrant setting filled with holiday cheer, making it easy to browse and enjoy the variety of goods on display. Whether you’re looking for stocking stuffers, one-of-a-kind presents, or simply want to get into the spirit of the season, this event has something for everyone.

Plus, with plenty of convenient on-site parking, attending is hassle-free. Bring your friends and family and enjoy a fun, festive shopping experience at one of the area’s favorite holiday craft fairs!