Pumpkin Picking Guide! - Westport Moms

Pumpkin Picking Guide!

Costumes are ordered (or will be soon=)), spider webs are out, and now we need pumpkins to decorate! Here is your Fall 2021 PUMPKIN PICKING GUIDE to the best family friendly recommendations in CT! Halloween may look a bit different this year once again, but that doesn’t mean we cant still enjoy pumpkin picking and some outside time with family and friends!

In addition to pumpkins, many of these wonderful farms also offer things like petting zoos, photo op areas, cider mills, corn mazes & hayrides. Outdoor activities- here we come!

Bishops Orchard
Bishop’s Orchards is an agricultural operation in Guilford, Connecticut, that serves as a farm, retail market, tourist attraction and winery. Bishop’s Orchards began operating as a family farm in 1871. Kids can enjoy a Corn Maze now through the end of October (weekends, 10-5pm). Open 10am-5pm everyday

COVID PROTOCOLS: You are NOT required to wear a face mask while at our PYO fields, but please try to maintain a 6’ social distance from other picking groups. Social distancing will be maintained, 6’ between individuals/groupsPicking containers will be provided—you are not allowed to bring your own container(s). The number of pickers in the field will be limited at any given time to allow for safe social distancing—these limits will vary depending upon the field and/or the amount of ripe berries within the field.

Address: 1355 Boston Post Rd, Guilford, CT 06437 – Just under 1 hour from Westport

Blue Jay Orchards
Blue Jay Orchards is a picturesque 140 acre farm nestled in the quaint New England town of Bethel, Connecticut.  It is one of the very few remaining commercial orchards in Fairfield County. They offer apple picking, a pumpkin patch and wagon rides. Reservations are not required, and there is no admission or parking fee. Open everyday from 10am-5pm

COVID PROTOCOLS: We will not be requiring our customers to wear masks,  and ask for everyone to respect the  individual preferences of our patrons. A bag must be purchased prior to entering the orchard for picking. Due to COVID concerns we are not offering wagon rides or our bee hive display this season as we want to respect social distancing guidelines.

Address: 125 Plumtrees Rd. Bethel, CT 06801 – Approx 30 minutes from Westport

Castle Hill Farm
Visit Castle Hill Farm this fall and take a walk through their patch! They have over 40 different varieties of pumpkins and gourds to look through! Hayrides and an epic 7-acre corn maze (don’t worry, you get a map!). Open Saturday & Sunday 10am-5pm

COVID PROTOCOLS: If you are sick or not feeling well, please do not come to the farm stand or other activities. Masks are required while on the farm premises. PET POLICY: Dogs are permitted on the farm, however, must be FRIENDLY, cleaned up after (even within trees, wooded area, and tall grasses, etc.), leashed, and quite.

Address: 25 Sugar Lane, Newtown, CT 06470 – Approx 30 minutes from Westport

Ellsworth Hill Orchard & Berry Farm
Located in the scenic Litchfield Hills, this family-owned and operated farm lets you pick your own strawberries, cherries, raspberries, blueberries, peaches, plum, sweet corn, pears, apples, pumpkins and gourds. They also have hay rides, an amazing corn maze and a vintage train set for the kiddies to play with. Open Monday-Saturday: 9am-6pm and Sunday 8am-4pm

Address: 461 Cornwall Bridge Rd. Rte.4, Sharon CT – Approx 1 hour 30 minutes from Westport

Harris Hill Farm
Harris Hill Farm has been the area’s premier pumpkin grower for more than 20 years.  On weekends during the month of October, they open their farm to the community and offer a pick-your-own pumpkin patch.  They also invite their guests to enjoy corn trivia, a ride on their hay wagon and to meet the farm animals in their barns. They specialize in large, high quality, jack-o-latern style pumpkins. Open from 10 am to 5:00 pm Saturdays & Sundays

Address: 106 Ridge Road, New Milford CT 06776 – Approx. 1 hour from Westport

Jones Family Farm
A Westportmoms favorite! Established in 1848, this 400-acre farm offers pick-your-own strawberries, blueberries and pumpkins with farm animals, hayrides, corn maze, fall flowers, fresh apples and piles of autumn squash. Pumpkin season is located at Pumpkinseed Hill at 120 Beardsley Road in Shelton. Open from 10 am to 5:30 pm. 

Address: 120 Beardsley Road Shelton, CT 06484 – Approx. 30 minutes from Westport

Lyman Orchards
Established in 1741, the farm is located on 1,100 acres in the beautiful Connecticut River Valley. You’ll find apples, pears, pumpkins and more. The Apple Barrel offers fresh baked pies, apple cider donuts, muffins, cookies, breads, pastries and more desserts. Apple barrel is open 9am-7pm daily.

COVID PROTOCOLS: Face coverings are recommended for Unvaccinated guests and employees when unable to maintain 6’ between you and others. Social distancing is to be maintained between guests. We have enhanced sanitation practices, regularly cleaning and sanitizing high touch points. You are requested to wash and/or sanitize your hands prior to entering the field, using the wash station or sanitizer. Picking containers are provided—you are not allowed to bring your own container(s).

Address: 32 Reeds Gap Rd. Middlefield, CT 06455 – Approx. 1 hour from Westport

March Farm
March Farm is a fourth generation family farm destination offering seasonal Pick Your Own apples & pumpkins along with family friendly activities. The Farm Store & Bakery is stocked with farm grown produce, regional food specialties and fresh baked goods – everything you need to compliment your next meal or desert. Enjoy family friendly activities including: (Hill Top Corn Maze, Pond Side Animal Yard, Hayloft Playscape & Pavillion) Open Everyday 10am – 6pm

No pets are allowed. 

Address: 160 Munger Lane Bethlehem, CT 06751 – Approx. 1 hour from Westport

Silverman’s Farm
Go enjoy their five-acre Animal Farm, visit their Country Market and pick your own pumpkins. Conditions change daily, so please call before coming for picking conditions! Currently available at their farm market – daily-fresh baked pies, cider donuts and baked goods, local honey, syrups and more! Animal farm will be open daily till Christmas (weather permitting) Open daily 9am-5pm.

Address: 451 Sport Hill Rd, Easton, CT 06612 – Approx 20 min from Westport

Do you have a favorite Pumpkin Pie, Bread, Soup or Seed recipe?? Please leave a comment and share a link!

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