There’s something magical about the way Rehoboth Beach comes alive for the holidays. As the air turns crisp and the town lights begin to sparkle, locals and visitors alike gather to celebrate the spirit of the season. From film and art to festive lights and seaside charm, November marks the start of one of the most enchanting times of year at the beach.
✨ Rehoboth Beach Independent Film Festival — November 3–9
For over two decades, the Rehoboth Beach Film Society has brought a world of storytelling to the Delaware coast. The annual Rehoboth Beach Independent Film Festival is a weeklong celebration of independent cinema, featuring thought-provoking documentaries, international films, and award-winning shorts. Whether you’re a casual moviegoer or a dedicated cinephile, this festival offers a rare chance to see exceptional films that inspire, challenge, and entertain—all right here by the sea. Screenings take place across several venues in town, creating a vibrant hub for film lovers to connect and share their passion.
🎅 Schellville Enchanted Winter Celebration — Opens November 22
Get ready to step into a true winter wonderland! The Schellville Enchanted Winter Celebration returns bigger and brighter than ever, transforming a corner of Rehoboth into a glowing holiday village filled with magic. Enjoy dazzling light displays, local artisan vendors, live entertainment, cozy fire pits, and festive bars serving seasonal cocktails. Families will love the snow zone, maze of lights, and holiday train rides, while adults can unwind in the heated lounges and “Enchanted Dining” experiences. The best part? Admission is free, making it the perfect outing for visitors of all ages.
🌟 Rehoboth Beach Christmas Tree Lighting — November 28 at 6:30 PM
Nothing says “the holidays have arrived” quite like the annual Christmas Tree Lighting at the Rehoboth Beach Bandstand. Gather with friends, family, and neighbors for this cherished local tradition that officially kicks off the holiday season. Enjoy live music, sing along to your favorite carols, and watch as the town’s towering Christmas tree lights up the night sky. The energy, laughter, and community spirit make it one of the most heartwarming nights of the year.
October might just be the best time of year to enjoy Rehoboth Beach with your pup. The weather cools down, the summer crowds ease up, and best of all – starting October 1 dogs are officially allowed back on the beach and boardwalk. Whether your four-legged friend loves a long walk, a lively festival, or just lounging by your side while you sip a drink outdoors, Rehoboth has plenty to offer this fall.
🏖️ Beach & Boardwalk Adventures
From October through April, dogs are welcome all day long on both the beach and boardwalk. That means endless opportunities for:
Long strolls along the shoreline.
Playtime in the sand and surf.
Exploring shops where many owners leave out water bowls and treats for visiting pups.
🍦 Pup Treats & Dog-Friendly Stops
Rehoboth is a doggy paradise!
Salty Paws – A doggie ice cream bar where pups can enjoy safe flavors like peanut butter, bacon, and seasonal pumpkin.
Critter Beach – They carry everything from healthy treats to grooming supplies, plus toys if you forgot to pack one for the beach.
P.U.P.S. of Lewes – In this welcoming boutique you’ll find all kinds of treats, toys, and accessories for dogs, cats, and their human pals.
Downtown Shops – Many small businesses keep treats outside and behind the counter!
🌳 Scenic Trails & Nature Walks
For a change of pace from the beach, Rehoboth has great trails to explore:
Junction & Breakwater Trail – A six-mile stretch connecting Lewes and Rehoboth, perfect for a leisurely hike through wetlands and wooded areas.
Gordons Pond Trail – Part of Cape Henlopen State Park, this boardwalk-style path offers sweeping dune and ocean views and — if your dog likes to bird-watch — plenty to keep your pup entertained!
🎃 Dog-Friendly Festivals & Events
October is festival season in Rehoboth Beach, and many events welcome dogs (or even celebrate them outright). Here are a few highlights:
Sea Witch Festival – October 24–26
One of Rehoboth’s signature events, Sea Witch is a full weekend of parades, vendors, and live entertainment. The costumed dog parade on Sunday is always a favorite — think wagging tails, creative costumes, and plenty of photo ops.
Bark on the Boards – October 18
This pup-centered celebration takes over the beach and boardwalk with dock-diving competitions, dog yoga, a costume contest, and vendor booths. Entertainment at the Bandstand keeps things lively, and the event is designed with dogs in mind – All in support of the important work at the Brandywine Valley SPCA!
🍂 Patio Dining With Pups
Cooler temperatures make October perfect for patio dining. Many Rehoboth restaurants welcome dogs outdoors, some even offering water bowls and treats. Grab a cocktail, order some fresh seafood, and let your pup enjoy the breeze at your feet.
Ever wonder what’s happening in Rehoboth Beach this Fall? We’ve put together a list of Rehoboth‘s favorites – among tourists and locals alike!
Local Favorites
The Seawitch Festival
The Sea Witch Festival is a Rehoboth Beach favorite, featuring a lively parade, live music, and plenty of Halloween fun. It’s the perfect way to enjoy the beach town’s festive fall spirit.
From deals at downtown boutiques and galleries to the nearby Tanger Outlets, Rehoboth has it all. Whether you’re hunting for unique gifts or beachside treasures, there’s something for everyone!
Enjoy vibrant markets thanks to Rehoboths bustling arts scene. Both the Rehoboth Beach Farmers Market and West Side Creative Market are perfect spots to browse, snack, and experience the town’s creative spirit.
Rehoboth Beach offers fantastic entertainment year-round, from live music at nationally recognized bars like The Starboard to award-winning theater at Clear Space Theatre. There’s always something fun happening!
Enjoy seasonal specials at most restaurants and bars, with fewer crowds and perfect weather for outdoor dining! Savor fresh outdoor dining at the Back Porch Cafe or indulge in seasonal specialties at Bodhi Kitchen.
September is one of the best times to visit Rehoboth Beach. The summer crowds begin to fade, the weather is perfect for beach days, outdoor activities, and the local calendar is packed with events, festivals, and live entertainment. Whether you’re a foodie, music lover, art enthusiast, or just looking for some seaside fun, there’s something for everyone this month.
Event Highlights
September 6 – Bethany Beach Boardwalk Arts Fest
Discover local and regional artists as you stroll the Bethany Beach boardwalk. From fine art to unique crafts, this is a perfect day to take home something special.
September 17–21 – Rehoboth Bear Weekend
A lively celebration of the Bear community featuring events, parties, and gatherings across town.
September 18 – Lewes Canalfront Concert Series
Enjoy live music on the waterfront in Lewes, just a short drive from Rehoboth.
September 18–28 – POTUS at Clear Space Theatre
Don’t miss this sharp and witty Broadway comedy during its limited run in downtown Rehoboth Beach.
September 20 – Mrs. Roper Romp
Dress in your best Three’s Company–inspired outfit and join the colorful crowd for this one-of-a-kind romp.
September 20 – Delaware Seafood Festival
A must for seafood lovers! Sample fresh catches and coastal favorites while enjoying live music and family activities.
September 26–28 – Foodees Food & Culture Festival
Celebrate international cuisine and cultural performances during this delicious weekend festival.
Save The Date
October 1 – Dogs Allowed on the Beach & Boardwalk
One of fall’s favorite traditions! Starting October 1, dogs are once again welcome to enjoy the sand and surf.
Weekly & Ongoing Events
Every Tuesday – Rehoboth Farmers Market
Fresh produce, baked goods, flowers, and local specialties.
Every Monday & Friday – West Side Creative Market
A great spot to shop handmade goods, art, and crafts from local makers.
Every Friday & Saturday – Piano Bar at The Pines
Cozy up with cocktails and sing along to live piano performances.
Every Monday, Thursday, & Friday – Karaoke at Purple Parrot
Belt out your favorite tunes at one of Rehoboth’s most iconic karaoke nights.
Every Saturday – Decade 80 Band at Nalu Dewey
Dance the night away with live music from the ultimate 80s throwback band.
Plan Your September Getaway
From food and arts festivals to concerts, theatre, and nightlife, Rehoboth Beach shines in September. Add in cooler evenings, stunning sunsets, and fewer crowds, and you’ve got the perfect recipe for a fall getaway.
Make your trip even more memorable by staying at The Homestead. Our welcoming atmosphere, comfortable accommodations, and convenient location make us the perfect home base for exploring all that Rehoboth Beach has to offer this fall.
The Rehoboth Beach Sea Witch Festival begins Friday October 25, 2019. This is an annual tradition held for now 30 years! For a full list of events, check out the Sea Witch Festival Website. Some must sees are the parade on Rehoboth Avenue beginning at 10am on Saturday and the Doggie Parade on Sunday at 10am.
We want to welcome to Delaware our newest neighbors, Larry and Lillian! This wonderful couple stayed at the Homestead B&B at the end of last year. During that stay they told us they were interested in making Rehoboth Beach their second home and they learned that we (Joe and David) are REALTORS with Joe Maggio Realty.
We showed them a number of homes. We also previewed properties for these clients and took video of several so they could better decide if seeing a house in person was worth the trip. Over the course of 10 months we waited till the perfect home came on the market and placed their offer. Fast forward 36 days later and they settled on that perfect house! It was such an honor to represent them.
Our raised vegetable boxes are finally built and filled. Got some fall crop seeds in and of course we grabbed 12 tomato plants, a few bell pepper plants, and six-pack of cucumber plants.
We’ll see how it goes. It took longer than expected to get them ready, but they look great. Next year we’ll be rocking and rolling for sure!
The last few weeks have been a whirlwind as we prepare for the next two months at the B&B. On the real estate front we have been equally busy closing 7 homes over the last 30 days. We had the absolute pleasure helping this wonderful family sell their former home and buy the next perfect home in Milton, DE. A few months ago one of their girls gave us a beautiful piece that she colored of pink flamingos because it reminded her of the Joe Maggio Realty for sale sign in their yard. It’s so amazing that we get to help families and make new friends at the same time!
Last night we were proud sponsors of pride night at Ryans Mini Golf. Pictured are Joe and David along with two buddies mid way through 18 holes. David won by a stroke! Proceeds benefited Delaware Pride.
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