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Best Events in Coastal Delaware This October: Festivals, Food, and Fall Fun

October at the Delaware Beaches is packed with fall fun — seafood crawls, wine dinners, haunted tours, live jazz, and Sea Witch weekend. Find the best events and plan your perfect autumn outing!

Welcome to The Tide Report! 🌊 Each week, we’ll catch you up on what’s happening around Coastal Delaware-from local news and exciting new developments to can’t-miss events and inside scoops. Whether you live here or just love spending time at the beach, this is your go-to for staying in the loop. Let’s dive in!

  • Talk of the Town

    • Best Events in Coastal Delaware This October

  • Inside Scoop

    • Coastal Delaware Hotels That Ranked Among the Best in the U.S.

    • Celebrate Oktoberfest 2025 in Coastal Delaware

  • Developments

    • Get Ready for The Granary

    • Quick Move-In Homes in Milton & Lewes

  • Exciting Events

    • History Book Festival

    • Dewey’s Golden Jubilee

    • 86 Hook & Ladder Brewfest

    • Andrew Sords at Milton Theatre

    • Spooky Bookish Earring Workshop

    • Negroni Week at Chesapeake & Maine

  • Featured Listings

Best Events in Coastal Delaware This October

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October might just be the best time of year at the Delaware Beaches! From seafood crawls and wine dinners to maritime festivals, haunted tours, live jazz, and the always-popular Sea Witch weekend, there’s something happening almost every day. Whether you’re looking for a fun date night, a family outing, or just an excuse to enjoy the crisp fall air, this guide will help you plan the perfect October around town.

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Coastal Delaware Hotels That Ranked Among the Best in the U.S.

Looking for the perfect place to stay at the Delaware Beaches? Four local hotels just ranked among the top 200 in the entire U.S. - and it’s all thanks to the amazing sleep experience they offer guests. These stays are getting rave reviews for comfort and relaxation. You’ll want to see which ones made the list and get all the insider information at our blog linked below!

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Celebrate Oktoberfest 2025 in Coastal Delaware

Oktoberfest season is here, and Coastal Delaware is turning into a fall festival playground! From parties in Lewes (think stein-hoisting, live music, pretzel crafts, and German-inspired eats) to Bavarian dinners, pop-up events, and weekend fests across Ocean View, Milton, and Millville, there’s a celebration every weekend.

Our complete guide is split into two blogs - labelled as Part 1 and Part 2 - with the first post covering all the kick-off events like Crooktoberfest, and ThompsonFest. Part 2 dives into OktoBearFest, Bankstoberfest, Oktoberfest dinners, and even more local flair for all to enjoy. Check out both posts and get ready to plan your ultimate Oktoberfest weekend all local here in Coastal Delaware!

Get Ready for The Granary

Big news for anyone dreaming of a new home near the beach! The Granary is a brand-new community coming soon to Milton, offering beautiful ranch and two-story homes with open layouts, 2–5 bedrooms, and plenty of space to make your own. You’ll love the modern finishes - think quartz counters, stainless steel appliances, and smart-home features -plus community perks like walking trails, a pool, playgrounds, and cozy gathering spots.

All of this is just minutes from downtown Milton and a quick drive to the Delaware beaches, in the highly rated Cape Henlopen School District. It’s the perfect blend of convenience, nature, and coastal living! If this sounds like the lifestyle you’ve been looking for, let’s schedule a call and talk about getting you on the list early.

Newport Slab (Acadia Landing)

Savannah Slab (Heritage Creek)

Clearwater Slab (Acadia Landing)

Canton Basement (Heritage Creek)

Quick Move-In Homes in Milton & Lewes

If you’ve been thinking about making a move, now might be the perfect time!

Lennar just released 4 beautiful homes in Heritage Creek over in Milton that are completely move-in ready - you could literally have keys in your hand in just a few weeks. Prices start at $479,990.

Over in Acadia Landing in Lewes, there are 7 homes available that will be ready in September, October, and November, dependent on which property chosen, so you could be settled into your new home potentially before the holidays to enjoy them at the beaches. Prices start at $499,990.

If you are curious on any of the insider details on any of these opportunities, we would love to connect and see how we can help your beach house dreams come true!