Dewey Beach Travel Guide: Your Ultimate Itinerary for Sun, Food, and Fun

^{_{Note: This post contains affiliate links to the products that I use and trust. This means that I might receive a small commission (at no extra cost to you) if you make a purchase using any of my links below. See full disclosure here}}

Welcome to Dewey Beach: Where Chill Vibes Meet Coastal Thrills

Looking for a laid-back beach escape that still delivers energy, flavor, and unforgettable moments? You’re in the right place. Whether planning a weekend getaway or squeezing in a day trip between Fenwick Island and Rehoboth, Dewey Beach is your golden slice of fun. From dog-friendly sands to legendary crab cakes and live music under the stars, this guide will help you plan an itinerary you won’t forget. Let’s Dig In.

The Best Way to Spend a Day in Dewey Beach

Want to know how to get the most out of your time in Dewey? Easy. Here’s a quick hit-list:

• Start with sunrise at the beach: Calm, colorful, and uncrowded.
• Grab breakfast at Baked Coffee Bar: Coffee, pastries, and dog-friendly vibes.
• Midday paddleboarding on Rehoboth Bay: Rentals are right off Dagsworthy Street.
• Lunch at Woody’s: Crab cakes that deserve a standing ovation.
• Afternoon crush cocktails at The Starboard: Dewey’s signature drink.
• Dinner + Sunset at the Baywalk: Quiet, cozy, and totally romantic.
• Live music at Bottle & Cork: Local legends and national acts light up the night.

Why Dewey Beach Should Be On Your Travel Radar

There’s a reason Dewey keeps popping up on those “Best Small Beach Towns” lists. Actually, there are several. Here’s what makes this beachy spot worth the hype:

1. It’s Walkable and Worry-Free

Once you park, you can walk to everything: bars, the beach, the bay, and bites. There are no beach shuttle dramas or traffic headaches.

2. It’s Pet Friendly (Seriously!)

During the summer, dogs are welcome on the beach before 9:30 a.m. and after 5:30 p.m. Many restaurants, like Nalu Surf Bar & Grill, welcome pups with water bowls and treat jars.

3. The Food Scene is Low-Key Incredible

From freshly caught seafood to crispy hushpuppies and tropical cocktails, Dewey’s food hits that sweet spot between beach-casual and foodie-worthy.

4. There’s Always Something Going On

Live music, local events, and even dog parades( doodle or Golden lover)? Yep. Whether it’s a Saturday night show or a mellow Monday on the bay, you won’t be bored.

5. You Can Chill and Adventure

Want to kayak through salt marshes in the morning and dance in flip-flops at night? Dewey does both without missing a beat.

Morning: Sunrise + Salt Air in Dewey

Start early (yes, it’s worth it). There’s nothing quite like watching the sun peek over the Atlantic with sand between your toes and coffee in hand. The beach is quiet, dogs are welcome, and the lighting is golden perfection for Instagram.

Pro Tip: Bring a hoodie—it’s breezier than you’d think.

Mid-Morning at Dewey: Coffee, Treats & Exploring

Hit up Baked Coffee Bar for strong cold brews and sweet treats. Their sticky buns are dangerously addictive. Even better? There’s a shady patio perfect for people (and dog) watching.

From there, explore the beach town’s side streets or walk the bay loop. You’ll spot pastel cottages, blooming hydrangeas, and locals walking their dogs like it’s a community runway show.

Dewey Lunch: Crabby & Happy

Visiting Dewey and not eating at Woody’s Dewey Beach Bar & Grill would be a crime. Their famous jumbo lump crab cake sandwich is all meat, no filler, and pure magic. Pair it with Old Bay fries and a cocktail. Sit outside and soak up the salty air.

Pro Tip: Go early or late to avoid the lunch rush. Locals line up for this one.

Afternoon: Dewey Bay Vibes & Crushes

Walk to the bay side and rent a paddleboard or kayak from Delmarva Board Sports. The water’s calm, the views are stunning, and it’s a relaxing workout that doubles as a sightseeing tour.

After your water adventure, it’s time for Dewey’s signature drink: the Orange Crush. This juicy, citrusy cocktail is refreshing and dangerously easy to sip. The Starboard is the go-to spot. Lively, colorful, and always a vibe.

Evening: Music Under the Stars in Dewey

As the sun starts to dip, head toward the Baywalk for a peaceful sunset. Grab dinner at Victoria’s, a hidden gem with panoramic views. Try the pan-seared salmon or vegan calabacitas

Then follow the music to Bottle & Cork, Dewey’s iconic live music venue. From local bands to big-name acts, it’s a fun way to dance off that seafood dinner.

Plan Your Dewey Day Trip (or Weekend!)

Dewey Beach proves you don’t need a passport or a packed itinerary to have a great time. With its blend of chill beach energy, fun food finds, and postcard-worthy moments, it’s a perfect little escape on Delaware’s coast.

Ready to plan your trip? Pack your sunscreen, grab your pup, and hit the road. Dewey’s calling.

Pro Tip: Book early during summer weekends—Dewey is a favorite among locals and East Coast travelers alike. I’ve been to the beaches in the area many times. Curious about what other beaches are in the area? Read the blog Delaware Beaches: Insider Guide to Sun, Sand & Charm

Have a favorite spot in Dewey Beach that I missed? Drop it in the comments below or tag me in your photos!

Stay curious, stay hungry, and keep exploring!
–Beth