Hey South Shore, you showed up big! 🍂

Last week’s debut issue was an incredible kickoff, and we’re already feeling the hometown love. From Bay Shore to Patchogue, neighbors are talking, sharing, and planning their weekends together. That’s exactly what South Shore Digest is all about.

This weekend, we’re keeping the momentum going with food festivals, block parties, haunted nights, and cozy community events that make October on the South Shore the best time of year.

So grab your sweater, pour yourself a pumpkin spice latte, and let’s dive in, shall we!

Top 5 for the Weekend

Famous Food Festival (Deer Park)

Over 60 food vendors, live music, and interactive art take over Tanger Outlets for one of Long Island’s biggest food weekends. Come hungry and make a day of it — there’s something for every craving.
When: Fri–Sun, Oct 10–12 | 11 am–8 pm
Where: Tanger Outlets, Deer Park
Price: $ (Kids under 8 free)
Link: Event Details
Tip: Go early to snag shaded seating near the main stage.

Beautiful: The Carole King Musical (Oakdale)

A Broadway favorite celebrating the music of one of America’s great songwriters — from “You’ve Got a Friend” to “Natural Woman.” Perfect for music lovers or an uplifting date night.
When: Sat–Sun, Oct 11 & 12 (Matinee & Evening Shows)
Where: CM Performing Arts Center, Oakdale
Price: $$
Link: Event Details

Village of Brightwaters Block Party (Brightwaters)

A full afternoon of community fun as Brightwaters transforms its Village Square into a lively fall block party. Enjoy live music by Dirty Vice Band, No Request Band, and more. Plus food, family activities, and local vendors throughout the “Four Corners”.
When: Sun, Oct 12 | 12–5 pm
Where: Brightwaters Village Square
Price: Free
Link: Event Details

Haunted House & Grounds (East Islip)

Connetquot River State Park turns spooky with themed trails, glowing displays, and a full dose of fall atmosphere. It’s family-friendly during the day and perfectly eerie once the sun goes down.
When: Fri–Sat, Oct 10 & 11 | 7-9 pm
Where: Connetquot River State Park Preserve, East Islip
Price: $ (parking fee)
Link: Event Details

The Musical Box performs Genesis Live (Patchogue)

Step back into the golden age of progressive rock as this world-renowned tribute recreates Genesis’ 1973 tour with stunning precision — lights, costumes, and all. A must-see for fans of theatrical rock and live performances.
When: Sat, Oct 11 | 8 pm
Where: Patchogue Theatre for the Performing Arts, Patchogue
Price: $$+
Link: Event Details

📢 Enjoying South Shore Digest?

We’d love your help spreading the word. Just forward this email to a neighbor, friend, or family member so they can join too.

The more locals we reach, the better this community guide becomes. Thanks for helping SSD grow!

New readers can subscribe free by clicking the signup link at the bottom.

Family Picks

Flip Circus (Bay Shore)

Big-top excitement returns with acrobats, clowns, and jaw-dropping acts under the red-and-white tent.
When: Thu–Sun, Oct 9–12
Where: South Shore Mall, Bay Shore
Price: $ (discounts available)
Link: Flip Circus

  • Free Kids Ticket: Use code KIDS2025 for one free child ticket (ages 10 & under) per paid adult (up to 4 kids per order).

  • 40% Off: Use FLIP40 during Facebook checkout for 40% off your total purchase.

Not So Scary Kids Adventure – Gateway’s Haunted Playhouse (Bellport)

Looking for Halloween fun without the fright? 👻
Gateway’s Not So Scary Kids Adventure is back with a daylight walk-through designed just for little ones! Explore friendly scenes, meet silly characters, and enjoy treats, games, and surprises in a not-too-spooky setting. Perfect for toddlers, preschoolers, and any kids who love Halloween magic without the jump scares!
When: Saturdays & Sundays, Oct 11–26 | 12–3 pm
Where: Gateway’s Haunted Playhouse, Bellport
Price: $$
Link: Gateway’s Haunted Playhouse

Long Island Columbus Day Parade (Town of Babylon / Deer Park)

Marching bands, local schools, and community groups fill the streets for Babylon’s annual Columbus Day Parade, followed by an Italian Food Festival at the route’s end. A lively, family-friendly tradition that celebrates local pride and heritage.
When: Sat, Oct 11 | 1 pm (opening remarks at noon)
Where: Parade starts at Deer Park Lake Avenue Firehouse, ends at Constantino Brumidi Lodge #2211, Deer Park
Price: Free
Link: Town of Babylon

Fire Safety Open House (West Islip Fire Department)

A fun and educational afternoon for the whole family. Meet local firefighters, explore fire trucks up close, and learn about fire prevention and home safety. Kids will love Sparky the Fire Dog and hands-on demos.
When: Sun, Oct 12 | 11 am–3 pm
Where: 309 Union Blvd, West Islip
Price: Free
Link: West Islip Fire Department

Date Night / Nightlife

Gateway’s Haunted Masquerade (Bellport)

Step into an unforgettable night of frights and fun with live entertainment, signature cocktails, and a haunted-house fast pass. Dress to impress for the Ultimate Costume Contest and brace yourself for the spine-tingling Coffin Ride.
When: Fri, Oct 10 | 6:30 pm
Where: The Gateway’s Haunted Playhouse, Bellport
Price: $$+ ($125 after early bird)
Link: The Gateway’s Haunted Playhouse

Weekend at Stereo Garden (Patchogue)

Patchogue’s biggest stage is going all-in this weekend with three back-to-back nights of live energy:

  • Fri, Oct 10: Funk Flex – New York’s legendary DJ brings nonstop beats from 9 pm–3 am.

  • Sat, Oct 11: Halloween Thriller Fright Fest – Costume contests, DJs, and spooky vibes.

  • Sun, Oct 12: El Reencuentro Tour: La Factoría & Eddy Lover – A night of classic reggaetón hits.

When: Fri–Sun, Oct 10–12
Where: Stereo Garden, Patchogue
Price: $$ - $$+
Link: Stereo Garden

Coco Montoya – Blues Guitarist (Bay Shore)

A soulful night of masterful guitar and smooth blues vocals as Grammy-winning artist Coco Montoya takes the stage. Perfect for a laid-back date night or music lovers who appreciate real live sound.
When: Fri, Oct 10 | 8 pm
Where: Boulton Center for the Performing Arts, Bay Shore
Price: $$+
Link: Boulton Center

Free & Affordable

  • Craft Buffet (Islip Library, Islip): A fun night of teen crafting with take-home goodies and snacks. Thu, Oct 9 | 6–7 pm. Free (registration required). More Info

  • Weekend at Loughlin Vineyard (Sayville): Relax among the vines with free live music and local bites all weekend long. 4 Days, 4 Events! Thu: Trivia Night • Fri: Sunset in the Vines • Sat: Swing & Sip (feat. Greg Bové) • Sun: Live in the Vines (Star Harbor). Free admission; wine and food available for purchase. More Info

  • Shooting Star (Patchogue): A witty and heartfelt romantic comedy about second chances, performed by St. Joseph’s University’s Clare Rose Playhouse cast. An intimate show that’s easy on the wallet and perfect for a cozy night out. Fri–Sat, Oct 10 – 11 | 8 pm & Sun, Oct 12 | 3 pm. More Info

Fresh Local Highlights

Sandbar Kitchen Cocktails & Entertainment (Patchogue)

This waterfront favorite pairs coastal cuisine with upbeat nightlife. Enjoy seafood classics, house cocktails, and live music almost every night — from acoustic sets to full band lineups. October brings outdoor fire pits, local acts, and dockside views that make it a perfect fall hangout.
Click Here: To see Sandbar’s menu & live band schedule

Roadtrip (Bay Shore)

A vibrant, Americana-themed restaurant and bar offering comfort food with a twist — from stacked burgers to shareable apps inspired by roadside diners across the country. Live music and weekend brunch keep things buzzing.
Click Here: To check out Roadtrip’s menu

Bar Lucy (Bay Shore)

Downtown Bay Shore’s newest cocktail lounge brings a splash of Miami-meets-Long Island energy to Main Street. Expect craft cocktails, DJ nights, and small plates in a sleek, coastal-modern space.
Click Here: To explore Bar Lucy’s menu & vibe

📌 Community Board (Quick Hits)

  • The Great Give Back @ South Shore LibrariesOngoing through October. —  Drop off donations or take part in community drives at local libraries in Babylon, Islip, Bay Shore, and Patchogue as part of this county-wide volunteer initiative.

  • Farmers Markets (Babylon, Islip, Bay Shore, Patchogue) – Ongoing weekends. — Shop local and support South Shore growers, bakers, and artisans at weekly farmers markets across our towns.
    Babylon     •     Islip     •     Bay Shore     •     Patchogue

That’s a wrap for this weekend, South Shore!
If you found a new favorite spot or event, share this issue with a friend. That’s how our little local guide keeps growing.

💛 Love it? Share it. Forward this email to a friend who would enjoy local picks too.
📬 Not subscribed yet? Sign up FREE here.
📸 Got tips or photos from an event? Email us at [email protected]

📲 Follow us on social — just click the icons below. 👇

Keep Reading