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Fun October Events Near Bear, DE: Fall Festivals, Trails and Trick or Treat

Oct 7, 2026

Your Autumn in Delaware Bucket List

It’s finally spooky season in Bear, DE, and there are tons of activities and events to do before it gets too cold to go outside without a jacket.

Here is our breakdown of the coolest events* on our bucket list for the Halloween season. 

What is the best pumpkin patch near Bear, DE? 

Ten acres of pumpkins and a corn maze, a mile off Route 92.

  • Ramsey’s Farm: Fridays 1PM to 5PM, Saturdays and Sundays 10AM to 5PM at 440 Ramsey Rd, Wilmington. 
  • Pick your own pumpkin from a 10 to 12-acre patch, then work through the corn maze. Little kids get the Spookley Trail, which is sized for them.
  • Hayrides, barnyard animals, pumpkin painting, and a playground, plus apple cider donuts and a farm market stocked with Ramsey’s own Wagyu beef.
  • Bonfire nights run Friday and Saturday from 6PM to 9PM, with flashlight corn maze and extended evening hayrides. Last entry is 7:30PM.

Where can the kids trick-or-treat near Bear, DE?

Newark closes Main Street for the ultimate Halloween parade and candy one-stop shops before the big night on the 31st. 

  • Newark Halloween Parade and Trick or Treat Main Street: Sunday, October 25 on Main Street in Newark.
  • Marching bands, floats, antique automobiles, and costumed characters. The parade starts at Tyre Avenue and Main Street and heads west to College Avenue.
  • Trick or Treat Main Street follows, with goodies from downtown businesses and a pumpkin patch photo spot.
  • All municipal lots offer free parking, and Main Street stays closed throughout for the kids. Organizers ask that you leave pets at home.

What is the best fall market near Bear, DE?

The Hagley Craft Fair is one of our favorite annual traditions. 

  • Hagley Craft Fair: Saturday, October 17 from 10AM to 5PM and Sunday, October 18 from 10AM to 4PM in Wilmington. Now in its 47th year.
  • One ticket covers both days, plus admission to the du Pont family home and garden. Vendors set up outdoors across Hagley’s upper property and inside the Soda House.
  • Wood, pottery, jewelry, fibers, and metal, with a specialty food market and regional food trucks. Shuttles run throughout.
  • Enter at Buck Road East off Route 100. GPS: 298 Buck Road, Wilmington. Dogs are not permitted at this one.

Where can we spend a fall evening outside near Bear, DE?

Hayrides, fire pits and a bar, with the sun going down over the pond.

  • Fall Fun by the Fire at Mt. Cuba Center: an evening event at 3120 Barley Mill Road in Hockessin. Advance registration required and space is limited. 
  • Hayrides through the natural lands, ending at fire pits with s’mores.
  • A full bar, dinner options and lawn games, set on a vista overlooking Armstrong Pond.
  • Garden admission is included with your ticket, so come early and walk the gardens before the sun drops.

What else is happening in Newark this month?

  • Main Street Mile: Sunday, October 4. A one-mile course down Main Street, finishing with an afterparty at the Deer Park Tavern.
  • Glasgow Park Farmers Market: Thursdays from 3PM to 7PM at 2275 Pulaski Highway, wrapping up October 15. Cash, card and EBT accepted.
  • Catch the market before it closes for the winter. The last three Thursdays of the season are the best ones for fall produce.

Where should we go for fall foliage near Bear, DE?

Plenty of places offer autumn colors before winter hits the area.

  • Lums Pond State Park sits right here in Bear, with more than 17 miles of trail around Delaware’s largest freshwater pond. The Swamp Forest Trail loops the water through black cherry, sweet gum, and maple, crossing boardwalks and bridges. The Little Jersey Trail runs 8 miles and suits everyone.
  • Brandywine Creek State Park is the one worth the drive north. More than 14 miles of trail across the Piedmont’s rolling hills, with blue gneiss stone walls from the late 1800s still marking the old du Pont dairy fields. The Tulip Tree Trail runs 0.8 miles through Delaware’s first designated old-growth forest.
  • Hawk Watch Hill at Brandywine Creek is where the birders gather during fall migration, and October is peak season.

Where can we get some fall-themed coffee and drinks in Bear, DE after a yoga session? 

  • kaffé KARMA in Greenville runs a seasonal drink menu through the fall. A coffee shop by day, a yoga and meditation studio by evening, with gourmet toasts and smoothies in between.

Live Close to It All

Reybold’s communities in Bear, DE put Lums Pond, Glasgow Park and Christiana Mall within a short drive, with Newark and Wilmington just up the road.

The new Terrace Apartments at St. Andrews are available now, in one, two and three-bedroom floor plans with an assigned spot in the private garage for every home.

Life in the
First State

There’s a good reason we’re based where we are. Delaware’s rolling fields and sun-kissed beaches blossom with historic towns and cultural hotspots. World-class destinations are all a short trip away, and with generous tax benefits, you’ll save a lot, too!