You know that feeling when the beach crowds thin out, but the town’s just getting started? That’s fall in Rehoboth Beach. After Labor Day, something shifts – parking gets easier, dogs return to the beach, and the whole town exhales into festival season.
We’ve been watching these September and October rhythms for years now, greeting guests who’ve figured out what locals already know: fall might just be the best-kept secret on the Delaware coast. Here’s everything happening this season, plus the timing tricks that’ll save you from circling for parking or missing the good crab cakes.
September: When Summer Decides to Stick Around
Dewey’s Beach Party Goodbye – September 14
If summer had a going-away party, this would be it. Right on the sand at New Orleans Street in Dewey Beach, bands play while the sun sets and everyone pretends it’s still August. The whole thing runs from afternoon into evening, with that loose, sandy-feet vibe Dewey does best.
What nobody tells you: Bring a low beach chair or blanket and claim your spot by 4 PM. The rideshare from our inn takes five minutes and beats hunting for parking near the beach. Last year, a couple staying with us walked down with a cooler and made friends with half the crowd – that’s the Dewey way.
The Day Parking Becomes Free – September 15
Mark your calendar: September 15 is the last day for parking meters in Rehoboth. Starting September 16, those quarters stay in your pocket until next May. It’s like the town’s little gift to fall visitors.
Here’s the thing though: Free parking doesn’t mean empty spots. Rehoboth Avenue still fills up on nice weekends. Most of our guests just leave their cars here and walk the ten minutes to the boardwalk. Way less stressful.
Delaware Seafood Festival – September 20
Behind the Tanger Outlets from 10 AM to 5 PM, this festival is exactly what it sounds like – and then some. Yes, there are mountains of steamed crabs and towers of crab cakes. But there’s also:
- Live cooking demos where local chefs share tricks you’ll actually use
- Oyster shucking contests that get surprisingly competitive
- Kids’ activities that go beyond face painting
- Local craft vendors with stuff you won’t find on Amazon
- Beer gardens featuring Delaware breweries
From experience: Hit the crab cake stands before noon – the best ones sell out. Bring cash (not every vendor has gone digital), and wear sunscreen. That September sun still has some punch.
Dewey’s Golden Jubilee is back
Join Golden Retriever lovers from near and far in Dewey Beach for a weekend filled with parades, beach romps, social gatherings, and heartfelt traditions. From costume parades to memorial bonfires, it’s a celebration of our furry friends you won’t want to miss.
Dewey’s Fall Jubilee – Event Details
Friday, September 26
- 5:30–6:30 PM → Shirt Sale & Pick-Up @ Gerar Lake
- 6:45 PM → Costume Parade to Rehoboth
- 7:30 PM → Ice Cream Social @ Salty Paws
Saturday, September 27
- Location: Vandyke Street Beach
- 9:00 AM → Shirt Sale & Pick-Up
- 10:00 AM → Beach Romp
- 4:00–7:00 PM → Yappy Hour @ Mama Maria’s
- 7:00–9:00 PM → Memorial Bonfire @ Vandyke Street Beach (Oceanfront)
Sunday, September 28
- 11:00 AM → Farewell Gathering @ Hopkins Creamery
Official website
October: When Rehoboth Gets Its Personality Back
Dogs Return to the Beach – October 1
October 1 feels like a holiday for dog owners. Suddenly, leashed pups are welcome on both the beach and boardwalk through April 30. Morning walks become adventures. Evening strolls include four-legged friends. The whole town gets friendlier.
We’ve always been pet-friendly here at the inn (dogs get their own welcome treats), but October through April? That’s when Rehoboth truly becomes a dog town. The 7 AM beach walk crowd grows from a handful of early risers to a proper pack.
Local secret: The north end of the boardwalk, past the hotels, stays quieter for nervous dogs. Grotto Pizza’s outdoor tables welcome well-behaved pups. And that patch of grass by Grove Park? Unofficial dog meetup spot.
Fall Sidewalk Sale – October 3-5
For 48 years running, local shops have hauled their inventory onto the sidewalks for three days of deals. From 10 AM to 8 PM daily, Baltimore Avenue becomes an outdoor mall. Wilmington Avenue joins in. Even the Route 1 shops participate.
But here’s what makes it special: Delaware has no sales tax. So those markdowns? They’re actually markdowns. A guest last year scored a $300 jacket for $75. Another found handmade jewelry at half price. It’s like Black Friday with beach weather.
Timing tip: Friday morning has the best selection. Sunday afternoon has the best prices. Saturday? That’s when it feels like a block party.
Dewey Goes Pink – October 4
At 11 AM, hundreds of runners and walkers in pink gear take over Dewey Beach, starting at The Starboard. It’s a 5K run/walk plus a shorter fun walk, all benefiting the Delaware Breast Cancer Coalition. But calling it just a race misses the point.
This is Dewey doing what Dewey does: turning a good cause into a celebration. The post-race party spills onto the deck with live music, local food, and stories that’ll make you laugh and maybe tear up a little. Even if you’re not running, it’s worth watching.
Greyhounds Reach the Beach – October 9-12
Four days when retired racing greyhounds (and their humans) take over town. Sounds niche? Wait until you see 200 greyhounds in Halloween costumes parading down the boardwalk. Or witness the Blessing of the Hounds on the beach. It’s oddly moving.
The schedule includes:
- Thursday: Meet-and-greets at various venues
- Friday: Educational seminars (surprisingly interesting even for non-greyhound people)
- Saturday: The famous boardwalk parade at 11 AM
- Sunday: Beach blessing ceremony
One October, we had twelve rooms booked by greyhound families. The lobby became an impromptu dog park. Nobody complained. How could you? These dogs have the calmest energy – former athletes enjoying retirement at the beach.
Rehoboth Beach Jazz Festival – October 16-19
Four days, multiple venues, world-class musicians. The Convention Center hosts the big names. The Rusty Rudder deck offers sunset shows. Smaller venues like Clear Space Theatre feature intimate sets where you’re close enough to see the musicians’ expressions.
Last year’s lineup included Grammy winners playing to crowds of 300. That’s the magic here – artists who fill arenas elsewhere play rooms where every seat’s a good seat.
Insider move: Buy tickets for one headliner show, then explore the smaller venues. Some of the best moments happen at the late-night jam sessions when musicians from different shows end up playing together.
Sea Witch Festival – October 24-26
This is it. The weekend Rehoboth waits for all year. Downtown becomes Halloween headquarters with two parades, vendor tents, live music, and enough costumed dogs to break the internet.
The lineup:
- Friday: Vendor setup, live music starts, excitement builds
- Saturday: The main costume parade at noon (get there by 10:30 for a spot)
- Saturday: Dog parade at 3 PM (pure joy in canine costume form)
- Sunday: 5K race, kids’ activities, final vendor day
We’ve seen elaborate family costumes that took months to plan. Dogs dressed as sharks, lobsters, and one memorable year – an entire doggy Supreme Court. The creativity hits different when it’s by the ocean.
Survival guide: Book your room in August. Seriously. The whole region fills up. Bring layers (October beach weather swings wildly). And if you’re entering the costume contest, go big – competition’s fierce.
The Fall Beach Rhythm
Here’s what seventeen falls in Rehoboth have taught us: September still feels like summer with training wheels off. October brings the sweet spot – warm days, cool nights, and a town that remembers how to relax. The ocean’s still swimmable (if you’re brave). The restaurants stop rushing. Conversations last longer.
Beach walks hit different when you need a light jacket. Sunrise comes later, so that 6 AM walk becomes 7 AM, then 7:30. The light turns golden earlier, making 4 PM feel special instead of rushed. Even the dogs seem to know they’ve got the good end of the deal.
Planning Your Fall Visit
After all these years of watching guests discover fall in Rehoboth, patterns emerge. The happiest visitors are the ones who:
- Book early for event weekends (especially Sea Witch and Jazz Festival)
- Pack layers – 75°F afternoons can drop to 55°F evenings
- Make dinner reservations – fewer tourists doesn’t mean empty restaurants
- Bring the dog – they’ll never forgive you if you don’t
- Stay flexible – the best fall moments here are rarely planned
We keep our rates reasonable through fall because we want people to experience this version of Rehoboth. The one where you recognize faces on your third morning coffee run. Where dogs outnumber strollers on the boardwalk. Where locals actually have time to chat.
One Last Thing
You could visit Rehoboth Beach in July, fighting for parking and restaurant tables, sweating through the humidity. Many people do. But September and October? That’s when this town shows you who it really is. The festivals are fun, sure. The events bring energy. But it’s the Tuesday morning beach walks, the Wednesday sunset dinners without waits, the Thursday afternoon naps on uncrowded sand – that’s the fall magic.
The Canalside Inn has rooms throughout fall, each one a short walk from everything on this list. Some overlook the canal. Others face the quiet street. All of them include the kind of welcome that makes you exhale when you walk in. Because that’s what fall in Rehoboth is really about – remembering how to breathe again.
Ready to experience fall in Rehoboth Beach? Check our availability for September and October below. Dogs welcome. Humans too.
