Mark two Saturdays on the calendar. October 8 and October 17. Both land at Warren Woods Town Park, nine days apart, and both are the biggest events most Warren residents will attend all year. One has been raising money the same way since the Nixon administration. The other didn't exist before 2024. If you want to understand what Warren actually is right now, you don't need a census report. You need to notice why the town needs both.
A Festival That's Been Fundraising Since Before Most of Its Volunteers Were Born
The Warren Volunteer Fire Company's Fall Festival runs October 8th and 9th at Warren Woods Town Park, rain or shine, from 10:00am to 5:00pm, and this year marks its 55th consecutive run. Do the math and the first one happened around 1971, back when a one-Saturday county fair was still the biggest social event a small Litchfield County town could throw.
The lineup hasn't drifted far from that original formula. Expect garden and antique tractor pulls, a pumpkin cannon, blacksmith and aerial demonstrations, chainsaw carving, a petting zoo, and a 500-foot zip line. The Women's Auxiliary runs the country store, and the main draw is still the WVFC's open-pit roast beef, alongside fresh-made apple pies, soups, cider, and cheddar by the pound. Every dollar spent at the gate goes back into the department itself, since the event is presented by, and benefits, the Warren Volunteer Fire Company directly, not a third-party charity.
There's a detail in the address that most people drive past without registering. Warren Woods Town Park sits on Brick School Road, named for the one-room Brick School that, according to the Warren Historical Society, holds the distinction of being the single-room schoolhouse with the longest record of continuous operation in the State of Connecticut. The fire company's festival isn't just old by Warren standards. It's happening on ground that's been central to the town's civic life since before Connecticut had paved roads.
Nine Days Later, a Different Warren Shows Up on the Same Field
Then comes October 17 and 18, when the same park hosts something that looks almost nothing like the fire company's fair. This is only the third annual Warren OctoberFest, held at the same Warren Woods Town Park on Brick School Road, running from Saturday morning through Sunday afternoon.
The morning opens with a 5K Cider Run, then shifts into an afternoon built around local breweries, wineries, food trucks, and artisans. There's no roast beef dinner or tractor pull. It's craft cider, live music, and vendor tents, which is to say it reads like an event designed by people who moved to Warren for the same reasons second-home buyers move to Litchfield County generally: the land, the quiet, and a version of rural life that still has good coffee and better wine.
Here's a side-by-side, for anyone trying to decide which weekend to circle first:
| Fall Festival (Oct 8-9) | Warren OctoberFest (Oct 17-18) | |
|---|---|---|
| Age of the event | 55th year | 3rd year |
| Run by | Warren Volunteer Fire Company | Independent organizers |
| Signature draw | Open-pit roast beef, tractor pulls | 5K Cider Run, craft breweries and wineries |
| Where the money goes | Directly funds the fire department | Not publicly specified |
| Feels like | A county fair that never modernized | A brewery festival that found a barn |
Neither event is trying to be the other. That's the point.
The Complex on Cornwall Road Explains the Second Warren
If you want to see where OctoberFest's audience lives when it's not at a festival, drive to the crossroads of Route 45 and Route 341, where the Warren General Store sits at what its own owners call the crossroads of Litchfield County. For years this stretch of Cornwall Road was, as one local paper put it, a row of mostly empty shops with no real center of town to speak of. That changed when longtime Warren resident John Favreau bought the buildings and renovated them into what's now known as Warren Town Center.
"My whole motive was to revitalize the center of Warren," he explained.
Favreau runs the general store himself. Next door, in the oldest of the three buildings, erected in 1820, is WKND, a clothing shop opened by David Asmar, a former fashion-industry professional who, like Favreau, relocated from New York City to Warren. Asmar has said the goal was a shop accessible to both year-round residents and weekenders, and the third building in the complex, Warren Works, gives remote workers actual desks instead of a kitchen table. Three buildings, three different answers to the same question: what does a small Litchfield County town need now that it didn't need fifty years ago.
The Old Warren Never Actually Left
None of this erased the older version of the town. Warren was settled in 1737 as part of Kent and incorporated as its own town in 1786, and it's nestled between the larger towns of Kent and Litchfield, having once actually been part of Kent before it broke off. It's the kind of place that, as locals sometimes note, was incorporated just three years after the Revolutionary War ended and has grown little since.
That slow growth shows up in how the Warren Land Trust spends its year. Last year's Trails Day hike led members to the Keith Family Preserve, a 73-acre property acquired in 2021 through a bequest from Joyce Keith, with a wooded ridgeline, wetlands, and a hemlock grove at its high point. In other years the group has organized a walk under the Hunter's Moon on the Willis Tanner Farm Preserve, the kind of low-key, dogs-on-leashes evening that never makes an event listing outside of Warren itself. The land trust isn't competing with the fire company or the cider festival for attention. It's doing the same work the town's founders were doing in 1737: deciding what parts of this place stay wild.
What's Actually on the Calendar This Week
Both versions of Warren are running in parallel right now, not just in October. On Wednesday, August 12, the town hosts a Bear Aware Forum with DEEP wildlife biologist Jason Hawley at Warren Woods, a very old-Warren kind of event, practical and unglamorous, aimed at residents who've started finding bears near their compost bins. Meanwhile, Warren Beach has been running its own small concert series all summer, with Travelin' Vin performing August 9 and On the Road Again scheduled for August 16, the kind of low-stakes weekend soundtrack that fits the newer, more leisure-oriented rhythm the general store complex helped bring back to town.
Neither the bear forum nor the beach concerts made headlines outside Warren. They're not supposed to. They're evidence of the same thing the two October festivals prove on a bigger stage: this is a town running two clocks at once, one set in 1737 and one set a few years ago, and somehow neither one has had to give way to the other yet.
If you're already living with that rhythm, you know it doesn't need explaining. If you're thinking about what it would take to join it, from finding a place near enough to Brick School Road to walk to the fall festival, to understanding what a lakeside or village property actually costs to hold onto here, that's a longer conversation. Andrew Murphy and the team at E.J. Murphy Realty have spent generations getting to know towns exactly like this one. Get your free home valuation with our Litchfield experts whenever you're ready to talk specifics.
