September Events in Delaware
September is back-to-school season, but that doesn’t mean that you can’t find a ton of fun just minutes away from your home. Within a short drive of Bear, you can browse a free festival at Glasgow Park, walk the state’s largest outdoor art show, toast the season in a colonial river town, and shop at a farmers market on your way home from work.
Here are some confirmed events* worth adding to your September calendar:
What is the best free family festival near Bear this September?
Delaware VegFest lands right down the road at Glasgow Park, and it’s a free event.
- Delaware VegFest: Saturday, September 26 from 12PM to 6PM at Glasgow Park, 2275 Pulaski Highway. Free admission.
- Plant-based food vendors, speakers, and live entertainment, plus fitness activities, wellness booths, and family-friendly attractions.
Where can we see art outdoors near Bear, DE?
Art is just around the corner in your neighborhood, the best way to spend any sunny afternoon.
- Brandywine Festival of the Arts: Saturday, September 12 from 10AM to 6PM and Sunday, September 13 from 10AM to 4PM in Brandywine Park, Wilmington. Admission is $5 per day and children under 12 get in free. It’s the largest outdoor arts festival in the state, with juried artists, live music, and a food court. Free shuttle parking runs from Incyte on Augustine Cut Off.
- Art on the Green: Saturday, September 26 in Battery Park, Historic New Castle. A diverse arts and crafts show on the Delaware River, perfect to pair with a dinner outside before the weather gets chilly.
What is a fun date night near Bear, DE in September?
Pair a series of drinks with some fun atmospheres for an exciting evening with the local community.
- Historic Odessa Brewfest: Saturday, September 12 in Odessa. VIP entry at 12PM, general admission from 1PM. Adults only. More than 50 breweries will be on the grounds of the Wilson-Warner House, with live music on two stages and a steinholding competition.
- A Taste of Coverdale: Thursday, September 24 from 4:30PM to 8PM at Coverdale Farm Preserve in Greenville. Guided nature strolls with conservation experts at 4:30, cocktail hour at 5, and a farm-grown dinner at 6. Proceeds support the Delaware Nature Society.
What should we do with the kids on a Sunday?
Newark Community Day is the area’s biggest free fall family festival, which makes it the perfect occasion to round out the month before the spooky season starts.
- Newark Community Day: Sunday, September 20 from 11AM to 4PM on the Green at the University of Delaware.
- There will be local musicians, a food court, fine art and craft vendors, community booths, and a children’s area with scarecrow making.
- Leave your pets at home. Organizers ask that you skip bringing them to the crowds and the heat.
What is there to do at Glasgow Park near Bear, DE?
- Glasgow Park Farmers Market: Every Thursday from 3PM to 7PM, running through October 15. Cash, card, and EBT accepted.
- You can expect fresh produce, baked goods, honey, jams, prepared foods, food trucks, and handmade goods from local makers. Vendors rotate week to week.
- Walking trails and open lawn for jogs, picnics, and family gatherings, with the historic Bank Barn and Frazer House on the grounds.
Live Near It All
Reybold’s communities in Bear, DE sit minutes from Glasgow Park, Christiana Mall, and I-95, with Historic New Castle and downtown Wilmington a quick drive north.
St. Andrews puts the outdoors at the center instead of the edges. Four scenic ponds, walking paths that loop the water, sports courts, community playgrounds, a picnic area, and a pool and cabana with lap lanes and a shallow splash area for the kids. Inside, the new community center adds a vaulted gathering hall, a catering kitchen, a dedicated gym, and a mirrored yoga studio, alongside a 24-hour fitness center and a clubhouse with a coffee bar and internet cafe.
Choose from Garden Apartments, the new Terrace Apartments, Promenade Townhomes, Vista Twin Homes, and Arbor Manor Homes, in one to three bedrooms. Select homes are pet friendly and include a private garage.
Lincoln Center’s new luxury townhomes in Bear, DE put you close to it all, with rooftop views to come home to just minutes from walkable shopping and retail.
*Event details change. Confirm dates, times, and tickets on each organizer’s site before you go.




