Autumn Festivals, Pumpkin Fun & Big Events; Your Long Island Weekend Planner for Friday October 3 – Sunday 5, 2025
Hello, October Weekend. Fall is officially in the air on Long Island, and this weekend (Oct 3–5) brings the perfect blend of crisp weather and excellent event options. Whether you’re after spooky thrills, classic car shows, street fairs, art and music, or family fun, there’s no shortage of options to pack in the weekend.
Let’s dive in – here’s your one-stop guide to making the most of the October 3–5 weekend on Long Island.
Quick-Glance Highlights
| Event | Type | When / Where | Why Go |
|---|---|---|---|
| Spooky Fest at CSTL | Halloween / family | Oct 3 onward, Rockville Centre | Haunted trails, costumed characters, spooky & not-so-spooky fun |
| Moonlight Market – LI | Night market / arts & curiosities | Oct 4, 4 pm–midnight, Yaphank | Live glassblowing, burlesque, vendors & music |
| SouthamptonFest | Village arts & culture festival | Oct 4, Southampton | Local art, performance, food & community flavor |
| Great Pumpkin Palooza | Pumpkin patch / farm fest | Oct 4–5, Manorville | Family-friendly attractions, corn maze, music |
| Massapequa Park Street Fair / LI Fairs | Street fair / vendor market | Oct 5, 10:30 am–4:30 pm | 200+ vendors, live music, kids’ fun zone |
| Bethpage Street Fair | Town fair / shopping | Oct 5, 10 am–5 pm, Bethpage | Local artisans, family shopping day |
| Car Show Long Island (TOBAY Beach Fall Classic) | Car show / automotive | Oct 5, 11 am–4 pm, TOBAY Beach | Hundreds of classic, exotic, and emergency vehicles; live music & family friendly |
| Concert: The B-52s & DEVO – “Cosmic De-Evolution Tour” | Concert / rock / ’80s nostalgia | Oct 5, 7 pm, Northwell Health at Jones Beach Theater | Big headliner show on Long Island’s big stage |
| Stereo Garden – Life of Agony, Jasta, Rollin’ Coffin | Rock / metal concert | Oct 5, 6 pm, Patchogue | For heavier music fans, an evening of intensity |
| Kevin James: “Owls Don’t Walk” Comedy | Comedy / theater | Oct 5, 7:30 pm, The Paramount, Huntington | A fun night out with a name comedian |
Friday, October 3
Morning / Afternoon
- Kick off Spooky Fest at CSTL in Rockville Centre. This seasonal Halloween-themed event opens on Oct 3 and runs through the season. Expect fun for all ages with spooky paths, exhibits, and costumed characters.
- Browse local galleries, coffee shops, or regional farmers’ markets (depending on your area).
Evening / Night
- Head to a local dinner + concert night (check The Paramount, Patchogue Theatre, local pubs).
- Join Moonlight Market in Yaphank starting at 4 pm: shop artisan vendors, see glassblowing demos, enjoy live music and even burlesque / dance showcases.
- For night owls: if ghost or haunted-walk tours exist locally, this could be a good night to start spooky weekend vibes.
Saturday, October 4
Morning / Midday
- Visit SouthamptonFest for a full day of arts, performances, local food, and culture in the village.
- Or head to a local farm or pumpkin patch (Great Pumpkin Palooza opens this weekend in Manorville).
- Explore small towns (Port Jefferson, Greenport) for boutique shopping, cafés, and fall scenery.
Afternoon / Early Evening
- Return toward central/southern Long Island for dining, winery tastings, or scenic drives through North Fork vineyards (if in region).
- Catch local open mic nights, gallery shows, or community performances (check your local chamber listings).
Night
- Continue the evening at Moonlight Market, which runs into the night.
- Or find a concert, comedy show, or theater production – local venues often run special weekend programming.
Sunday, October 5
Morning / Midday
- Massapequa Park Street Fair / LI Fairs from 10:30 am to 4:30 pm: stroll over 200+ vendors, food trucks, live music, kids’ zones, and more. Admission is free.
- Bethpage Street Fair also runs 10 am–5 pm in Bethpage — good for shopping and family time.
- Visit the Car Show Long Island – TOBAY Beach (11 am–4 pm). Great for car lovers and families, with music and trophy presentations.
Afternoon / Evening
- Cap off your weekend with The B-52s & DEVO – Cosmic De-Evolution Tour at Jones Beach Theater (7 pm). This is a major rock/pop nostalgia show and a centerpiece event for Sunday night.
- For fans of heavier music, check Stereo Garden (6 pm) in Patchogue for Life of Agony, Jasta, and Rollin’ Coffin.
- Or go for something lighter: Kevin James: Owls Don’t Walk at The Paramount (7:30 pm) for a comedy night to ease into the week.
Event Themes & Highlights
- Fall & Halloween Vibes: Spooky Fest (CSTL) is timed perfectly as October opens. Whether you prefer mild spooks or full haunt trails, it offers a range.
- Outdoor / Family Festivals: Pumpkin patch, street fairs, artisan markets – many open-air events to soak in autumn air.
- Music & Performance Anchors: The B-52s/DEVO show, local concerts, comedy – plenty of strong names to anchor evening plans.
- Car & Auto Culture: The TOBAY Beach car show is always a draw for gearheads or curious families.
- Local Flavor: SouthamptonFest, small-town weekend wandering, local galleries, and pop-up artisan markets offer community flair.
