"We will be open this weekend 10-5, staying open a bit longer so you can stop by on the way back from the Harwinton fair!" That's the line Farmer Jon at Deeply Rooted Farms posted on October 3, 2026. The same note gives the season's only end date as "sometime in the end of October," when the pumpkins run out.
The Harwinton Fair has fixed dates. The rest of Harwinton's fall mostly doesn't. The farm season ends when the field is picked over. The Historical Society's cemetery walk has a rain date, and its two listings give different start times. Most of the fall depends on timing.
The One Date That Won't Move
The 169th Harwinton Fair runs through Sunday, October 4, at 150 Locust Road. Sunday hours are 9 a.m. to 6 p.m. Admission is $10, children 12 and under get in free, and parking is free. Saturday runs late, until 9:30 p.m., with buildings closing at 9. South Road and Blind by Eight play the evening sets.
Sunday's schedule has the Matica Circus Youth Troupe, dirt-bike freestyle motocross, the draft-horse pull, a rabbit costume contest and the Litchfield County skillet-throw finals. The schedule is on the Harwinton Fair site.
One change this year affected exhibitors more than visitors. Entries could be submitted online, and entry was free for everything except the Horse Show. Organizers said the goal was less volunteer work, simpler entry and better sustainability. If you entered vegetables, baking or crafts this year, you went through that new system.
After Sunday at 6, the town's fall doesn't run on a printed schedule anymore. It depends on supply.
A Pumpkin Season Measured in Pumpkins
After this weekend, Deeply Rooted Farms keeps its pumpkin stand open weekends from 10 a.m. to 4 p.m. until the pumpkins are gone. The stand is the farm's old strawberry shack, one mile south of the Route 72 and Route 4 intersection on Route 72. It takes cash or credit, and dogs aren't allowed.
Here's what's in the field and what it costs, according to the October 3 update:
| What | Price |
|---|---|
| Wheelbarrow full of pumpkins | $80, same as last year |
| Using the handlebars as part of the load | $30 extra |
| Corn maze, new this year | $5 per person |
| Sunflower picking | $2 per person |
| Raspberries, expanded patch | $7 per pint |
| Winter squash box, 40-pound bushel | $37 |
| Individual pumpkins and small gourds | Sold by the pound |
The $30 handlebar charge is there because people load pumpkins past the rim and up the handles. The farm prices that extra space separately.
There are two large pick-your-own patches with many kinds of pumpkins and gourds. You pick off the vine and clip the stems yourself. One item is missing. "Fall strawberries this year will not be available as we had problems with the crop," the update says.
Why Early October Beats Late October
The farm says plainly that the season gets worse as it goes on.
"The most authentic experience is always in the beginning as the patch has not been picked yet."
The raspberries work the same way. The update calls this "a good fall raspberry year" and says serious pickers should come early on Saturday morning. The patch is bigger this year, but the best berries still go to whoever gets there first.
So "until the pumpkin supply runs out" has a practical meaning. The weekends right after the fair have the fullest patch and the longest hours. By late October you may find a mostly picked field, or the stand may already be closed. The farm doesn't promise a last weekend. The Deeply Rooted harvest calendar is where it posts updates.
Maple View Farm at 276 Locust Road, the same road as the fairgrounds, is another option. It's a certified-organic vegetable farm with a self-serve honor stand selling seasonal fruit, vegetables, flowers and eggs. A listing last updated in January 2025 gave the stand's hours as 8 a.m. to 8 p.m. daily, from mid-June through October. That's the most recent schedule available, and it predates this season. Late October may be the end of its run too. Over on Burlington Road, Echo Farm at number 167 is listed with a stand selling maple syrup, goat-milk soap, hay, plants, vegetables and candy. The listing gives no hours.
October 17 at South Cemetery
The fall's next fixed event isn't about the harvest. It's part of the Harwinton Historical Society's America 250 series, a year of programs marking the country's 250th anniversary. The series has already included the Stars, Stripes & Songs evening at the Town Hall Complex in July and a September talk by costumed historians on women's wardrobes in the Revolutionary era.
"Saluting Our Patriots: A Cemetery Walk" takes place Saturday, October 17, at South Cemetery. Costumed performers portray Harwinton Patriots and the town's founding residents. The rain date is Sunday, October 18.
The start time is unsettled. The town calendar lists the walk from 10 a.m. to 3 p.m. The Historical Society's program guide calls it an afternoon event. Neither lists a price or a route. If you want to hear every portrayal, check the time with the Historical Society that week.
The town has also posted a self-guided South Cemetery walk handout that uses a brochure and the grave markers. It's an older, separate document, and nothing says the costumed walk follows its route. It still works as background reading, or for a visit on another quiet weekend.
October 24 and the Candy-Bag Admission
A week later, Trunk or Treat runs Saturday, October 24, from 5 to 7 p.m. at the Town Hall Sports Complex. The town asks families to bring a bag of candy in place of an entry fee. Trunk-decorating registration is free and opened September 24.
That Saturday is also near the end of Deeply Rooted's stated window, which closes "sometime in the end of October." If you're planning to carve or decorate a trunk with pumpkins from Route 72, buy them on an earlier weekend. The patch may not last until the 24th.
The Calendar Through Veterans Day
The dates below are published. Everything else this fall depends on the weather or on what's left in the field.
| Date | Event | Where |
|---|---|---|
| Sun., Oct. 4 | Last day of the 169th Harwinton Fair, 9 a.m. to 6 p.m. | 150 Locust Road |
| Weekends through late October | Deeply Rooted pumpkin stand, 10 a.m. to 4 p.m., until supply runs out | Route 72, one mile south of Route 4 |
| Sat., Oct. 17 | Saluting Our Patriots cemetery walk; rain date Oct. 18 | South Cemetery |
| Sat., Oct. 24 | Trunk or Treat, 5 to 7 p.m. | Town Hall Sports Complex |
| Wed., Nov. 4, 7 p.m. | Harwinton Woman's Club America 250 quilt drawing | Harwinton Town Hall |
| Wed., Nov. 11, 11 a.m. | Veterans Day Ceremony | Harwinton Town Green |
The guide says winners of the Woman's Club quilt drawing will be notified. The Veterans Day Ceremony on the Town Green is sponsored by Harwinton Veterans. Four days later, on Sunday, November 15 at 2 p.m., Harwinton Congregational Church at 2 Litchfield Road hosts "Pulpits of Liberty," a program on the role Litchfield County churches played in the Revolution.
After Thanksgiving, the Fields Change Crops
Once the pumpkins are gone, the next harvest in town is Christmas trees. No 2026 schedules have been posted yet, so the details below are past practice for planning, not confirmed dates.
Deeply Rooted Farms' tree page describes a choose-and-cut operation with check-in at 91 Terryville Road. It lists Balsam, Canaan, Concolor and Fraser firs, plus spruce and white pine. The undated page gives hours of Fridays noon to 5 p.m. and weekends 9 a.m. to 5 p.m., from the day after Thanksgiving through December 24.
Barry Farms at 195 Mansfield Road is listed by the Connecticut Christmas Tree Growers Association as a choose-and-harvest farm. The association's 2024 profile shows it open daily from 9 a.m. to 4 p.m. during the season. It lists choose-and-cut Canaan, Balsam, Fraser and Concolor firs, pre-cut Nova Scotia balsams, and wreaths, centerpieces, ornaments and products from local artisans. The listing tells visitors to check the farm's own announcements for opening and closing dates.
So a pick-your-own Harwinton fall runs from Deeply Rooted's pumpkin patch on Route 72 to its tree check-in on Terryville Road. Barry Farms on Mansfield Road picks up around the same time.
At Litchfield County Real Estate, we plan our Harwinton photo and video shoots around this same calendar. Fall light over the fields, the fair week and the switch to tree season all show up in how a property looks on camera. If you'd like to talk about how your place shows in the Harwinton fall, Kristen Duchene and the team are a call away. Contact Us.
