First Fridays in Oxford
Yes, Oxfords First Fridays are not just a summer thing they go all the way through the fall and into December. This fun street fair has a theme for each month from harvests, to OASD pride to festive lights, car shows and more. They happen the first Friday of every month rain or shine and feature booths from local community businesses and organizations, great food, music and more. The event is free to attend and is open to all ages.
Yellow Springs Village Open House & Fall Festival
Pumkin painting, haunted houses, food trucks, local artists and vendors and more. This fall festival is a free event and one not to miss. Want to race a pumpkin, or enter into a jack-o-lantern competition? Its here! You are invited to tour the entire village and enjoy all it has to offer with activities and entertainment for every age. Come explore the historic haunted yellow springs village.
Third Thursdays in Kennett
Every third Thursday in Kennet through October there is open air dining. If you are looking for a fun night out with a unique twist try one of Kennett Square many participating restaurants and eat out under the stars.This event also features live music and the non-Dining shops are typically involved as well. This is a very popular event so reservations are highly recommended. Due to street closures I also recommend scoping out a route and parking ahead of time so you don't miss your reservation.Kennett Mushroom Festival
Normally in September you absolutely have to come to this event if you live in the area, it is the mushroom capital of the world after all. This is a family fun event that happens every year where the whole town shuts down the street and all the local vendors and business welcome you to walk the town and see what Kennett has. So mark your calendars and don’t miss it
Apple picking at Highland Orchards
Located in West Chester Highland orchards is the place to go for apple picking. With over 20 varieties of apples to choose from, fresh baked goods seasonal produce a corn maze and beer garden you cannot go wrong with a day spent at Highland orchards.Weekends typically will have some sort of event happening so make sure to check out their calander on their website for and updated list of all the fun activities they have planned.
Pumpkin Painting at the Vineyard
At Penn Wood Winery Grab a pumpkin from the patch & paint a spook-tacular masterpiece to display for Halloween! Pumpkins are $10 each to pick & paint (Limit: 1 pumpkin per person). Pumpkins are available on a first come, first served basis (no tickets or reservations required). This activity is open to all ages. Children must be supervised by an adult.
Enjoy wine tasting, wine by the glass & bottle, local beer, cider & bites.
The Sunflower fields at Gunther Farms in Downingtown
This hidden gem offers a great place for photos. If you are looking for the perfect fall family photo backdrop this is the place to go. It is free and is normally not too crowded during the week. Weekends can be difficult to find parking but this place is always open so no need to worry about hours. Be sure to get there early in the season as sunflowers start to die as the weather turns and days get shorter.
Pumpkin Picking at Lytles Farm
Tucked away in New London is Lytles Farm with the best pumpkin patch around. There's also a fun corn maze to get lost in and they are open from early September until November so you always have plenty of time to stop in and grab more pumpkins for every fall holiday there is. It does cost money to enter the corn maze for adults, but kiddos are free so bring them all along and let them have all the fun getting lost in the maze with you.
Kennett Brewfest
For $65 come spend the day in Kennet sampling brews from all the local breweries you can think of. With over 100 different breweries participating each year this is an event you do not want to miss. This is a 21 and over event and there are designated driver ticket prices which are deeply discounted.
Fun at Milkyway Farms
Open Fridays, Saturdays and Sundays, general admission tickets are required per person over 3 years old. With each general admission ticket, you may wander through the corn maze, take family photos, visit the farm animals, and stroll to one of our pumpkin patches through our farm meadow as part of your 2-hour experience. Or hop on one of the hayrides to a different pumpkin patch. There's more than just pumpkin here, grab all your vegetables, and honey products during your visit. Want a cool treat, try the Chester Springs Creamery, open for ice cream from 11am-8 pm.
Longwood Gardens
The pumpkin playground and garden railway at longwood is one not to miss. Longwood gardens is known for having some of the most beautiful gardens and shows year round so of course they have a special fall fun activity for you. Although this is not as well known as the winter light show, you will still have to reserve a time to participate and as always try to book early as they do sell out.
Bonfires and Hayrides at Sugartown Strawberries
Hayrides have popularly been reserved with bonfire/birthday party reservations at night to and from the fire's location and also for daytime school/organization field trips and picnics. Hayrides are around the entire farm (wildlife and nature landscapes included) and back to the picnic site near parking. Show up before the end of October to grab as many wagons as you or your family and friends need to walk to our pumpkin patches where you can pick your own pumpkins and experience the feeling of farm fresh!
West Chester Chili Cook off
Are you a chili lover? Then you cannot miss this event. Gay street is closed off every October and everyone enters their best chili recipe. Then we get to sample all of them and decide who has the best Chili. Bring the family and your appetite and come try some amazing local chilis.
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