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Perfect for weekend escapes, family celebrations, creative retreats, or simply enjoying time with friends, this historic home adapts to your needs. Three bedrooms, a full kitchen, and timeless architecture blend comfort with character, making every stay unforgettable.

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I asked ChatGPT to roast every town in Windham County, gently. Quiet Corner, prepare to laugh at your own zip code.

Ashford - “Directions: “Left at the stone wall, right at the other stone wall.”

Brooklyn - “Small talk here is 70% weather, 30% what you paid for fried dough.”

Canterbury - “Route 169: gorgeous drive, suspiciously few places to panic-pee.”

Chaplin - “Nightlife = your neighbor’s porch light and a chorus of crickets.”

Eastford - “Population: deer. Government: blinking yellow. Motto: “You’ll figure it out.”

Hampton - Goodwin State Forest: more trails than cell bars—on purpose.”

Killingly (Danielson/Dayville) - “Distance is measured in Dunkins and traffic circles.”

Plainfield (Plainfield/Moosup/Wauregan/Central Village) - “Truth in advertising: plain name, not-so-plain personalities.”

Pomfret - “Even the stone walls have legacy status.”

Putnam - “Antique shopping: retail therapy that weighs 200 pounds.”

Scotland - “Population: your group chat, give or take.”

Sterling - “Blink and you’re in Rhode Island buying gas you didn’t plan on.”

Thompson - “Speedway energy so strong even the stoplights feel judged.”

Windham/Willimantic - “Thread City: where plans unravel and frogs keep morale up.”

Woodstock - “Heading into town” still means Putnam; don’t lie.”

Hit reply and tell me if ChatGPT nailed your town
or drop your own spicy local one-liners, I’m all ears.

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SATURDAY 10/4

Thompson | 21st Annual Thompson Community Day | 11am-3pm - Join in the festivities of celebrating Thompson at Riverside Park (56 Market St). Performances from Thompson Public School groups, business of the year, a reptile show, martial arts demonstration, bounce houses, food truck, vendors, and a whole lot more. Even if you’re not from Thompson, it’s a great way to see what this town is all about!

🐶Adopt-a-pal: Meet Charley, a 1.5-year-old chinchilla with circus-level tricks and just enough mischief to keep you smiling. Give him a little time to trust you and he’ll go from shy fluff to headline act, best with patient adults or older kids.

🏡House of the week: A beautifully restored 1780 colonial with modern flair, think mahogany-paneled study, marble floors, and three fireplaces. It’s sitting on 11+ acres with a three-car barn to boot. It’s that once-in-a-generation home you tell your grandkids about. Check it out!

🥾Trail of the week: Moosup Valley State Park Trail in Plainfield/Sterling
A flat, easy rail-trail that runs 5.8 miles along the Moosup River. Park at the lot on Main Street in Moosup and head east for a quiet ride or walk under tree cover. Great for all ages, pups included, with fall colors starting to pop.

🔭Sky report: The Harvest Full Moon rises Monday night (Oct 6–7), big and pumpkin-colored as it clears the treeline, the perfect backdrop for any farm stand or corn maze selfie. The Draconid meteors technically peak Oct 8–9 (just outside our window), but keep an eye out late this week; you might catch an early streak zipping past the moonlight.

Moosup | Wellness Series: Gut Health | 6-7pm - Learn all about how much your gut health can affect your overall wellbeing. Make sure to register with Love & Light Healing Studio (5 Legacy Dr).

Willimantic | Paint Your Own Pottery | 6pm $ - Paint a mug and grab a pint at WilliBrew (967 Main St). Tix

LIVE MUSIC

⬢ Stomping Ground - Putnam | Mike Wood | 8-11pm

Pomfret | Blood Drive | 1-6pm - It’s a perfect day to help save some lives with a blood donation at First Congregational Church of Pomfret (13 Church Rd). Sign Up

Thompsons | Cruise Night | 4-9pm - The end of the Thompson Rod and Gun Club (93 Brandy Hill Rd) cruise nights is nearing. These last two weeks will see the addition of roast beef sandwiches available for purchase. Cash only

Woodstock | Medicare Enrollment Info Session | 10am - So, not too exciting, but if you know anyone that has questions about the Medicare Enrollment process, send them to Woodstock Town Hall (415 Rt 169).

TRIVIA

Stomping Ground - Putnam | 7pm
Bear Hands Brewing - Putnam | 6pm
Mill Town Grill - Thompson | 6:30pm
Hank’s - Brooklyn | 6:30pm

Ashford | Car Cruise | 5-8pm - We’re getting down to the last few cruise nights at Ashford Volunteer Fire Dept (46 Westford Rd). Touch-a-truck, 50/50 raffle, music, and more.

Danielson | NYPC Oktoberfest | 5-8pm - In case you needed an excuse to drink, NewYork PIZZA CO. (8 Furnace St) is holding a night celebrating the German event. Stein hoisting, pretzel swing and catch contests, and swag/giveaways.

North Grosvenordale | Learn To Pan Sear | 6-8:30pm $ - Learn to pan sear some seafood, make risotto, and improve your knife skills at New Boston Beef (17 Fabyan Woodstock Rd). Tix

South Windham | Textured Painting | 6pm - Make a textured ghost, black cat, or pumpkin at Guilford Smith Memorial Library (17 Main St). This is an adult program, sign up by calling (860) 423-5159 or email [email protected].

Willimantic | Gallery Opening | 7-9pm - Check out the vibrant works of artist Isyss Christina at The River Room (50 Riverside Dr). Complimentary refreshments and live music to go along with exhibit!

Willimantic | Psychic Mediumship Fundraiser | 7pm $ - Local medium Rebecca Anne LoCicero is doing a reading to help benefit the Windham Theatre Guild (779 Main St). If you’re interested, call (860) 423-2245.

Woodstock | Speed Dating 40s-50s | 5:30-7:30pm $ - If you’re in your 40s or 50s and are looking for love, Taylor Brooke Brewery is holding a speed dating event for singles in that age range. Your first drink is included with the ticket. Tix

LIVE MUSIC

⬢ Stomping Ground - Putnam | Straight Up Jazz Series | 5:30-7:30pm
⬢ Stomping Ground - Putnam | Ryan Leddick | -11pm

TRIVIA

Trolley Pub - Willimantic | 7:30pm
Midway Restaurant - Ashford | 7pm

Brooklyn | Haunted Barn/Corn Maze | 6-9:45pm $ - Carver’s Curse (329 Stetson Rd) is inviting you to a night of frights and fun, in their 20-room house of horrors, and continuing in the corn maze. Be forewarned, this isn’t something for children under 12. Tix

Dayville | QCPSG Whiskey Dinner & Fundraiser | 6-9pm $ - Help support the Quiet Corner Peer Support Group with an amazing 5-course dinner (the main course of Turf and Turf - Smoked brisket and steak tips), each course paired with high-end whiskeys. Black Pond Brews (1001 Hartford Pike) is hosting, with proceeds going to QCPSG. Tix

Hampton | Laugh For Life | 7pm $ - Enjoy three stand-up comedians and help support a local non-profit that focuses on providing aide to women dealing with unexpected pregnancies. Tix

Plainfield | Edgar Allen Poe Impersonator | 6pm - Kick off spooky season with an evening at Plainfield Rec (482 Norwich Rd). Learn all about the life and times of EAP, played by Campbell Harmon. If you sign up in advance, you might even win a prize!

Pomfret | Spooky Paint Night | 6-8pm $ - Pomfret Rec (207 Mashamoquet Rd) and Tunk City Revival are teaming up for an all ages paint night. Register

Putnam | Murder On The Orient Express | 7:30pm $ - Come see Hercule Poirot do what he does best at The Bradley Playhouse (30 Front St). If you haven’t been to any live theater, this is a great jumping off point! Tix

Putnam | Zombie Fashion Show | 7pm - The Frightfully Fabulous Zombie Fashion Show returns to Rotary Park (196 Kennedy Dr), with volunteers getting dressed to kill. If you want to participate, make sure to register by 11:59pm on 10/2. More info

Willimantic | Nightmare on Main | 7-9:20pm $ - Check out the annual Nightmares on Main Street, held at the Connecticut Eastern Railroad Museum (55 Bridge St). This is for people 12 and older, and is aimed at giving you some scares. $18/person, cash only.

Woodstock | Pirates of Penzance | 7pm $ - If you’re looking for a swashbuckling good time, head to the Loos Center for the Arts (150 Rt 169), for a production of this classic comedy. Tix

LIVE MUSIC

⬢ Woodstock Tavern - Woodstock | Hold My Beer | 6:30pm
⬢ Black Dog - Putnam | Big Lux | 7:30pm
⬢ Stomping Ground - Putnam | Jeremiah Tall | 8-11pm

TRIVIA

Taylor Brooke - Woodstock | 6:30pm

Ashford | Walktober at the Academy | 1:30-4:30pm - Now’s the time to check out the historical Ashford Academy (73 Fitts Rd), which was built in 1825! If you’re curious about the oldest building in Ashford, take advantage of this opportunity!

Brooklyn | Haunted Barn/Corn Maze | 6-9:45pm $ - Night 2 of Carver’s Curse (329 Stetson Rd) is inviting you to a night of frights and fun, in their 20-room house of horrors, and continuing in the corn maze. Once again, this is meant to be terrifying, so don’t bring the little ones. Tix

Canterbury | Riley Farm Rescue Halloween | 11:30am-3pm $ - Trick-or-treat around Riley Farm Rescue (13 Barstow Rd), wear a costume, enter to win raffle baskets, and check out some smashing pumpkins with the piggies. Tix

Mansfield | Wellness Connect CT Expo | 11am-3pm - So, technically not in Windham County, but, it’s right next door, so I’m putting it in here anyway. This joint effort from the Tolland Chamber and Windham Region Chambers of Commerce is a showcase of all things health/fitness/nutrition/wellness-related. Swing by East Brook Mall (95 Storrs Rd), if you’re interested.

Moosup | Fall Arts, Crafts, & Vendor Fair | 9am-2pm - This is the 2nd annual Arts, Crafts, and Vendor Fair at Rotary Park (Prospect St). Hang out and listen to live music, do a little shopping, and grab something to nibble on. There will also be dogs for adoption, in case you’ve been looking for a new furry friend.

Plainfield | Chestnuts and Overlooks | 10am-12pm - Go for beautiful hike through Pachuag Forest (70 Colbridge Rd), check out native chestnut trees (the husks look like land urchins), rock quarry remains, old foundations, and more. Hike is approx 2 miles. RSVP

Pomfret | Fall Festival | 12-5pm - We-Li-Kit Ice Cream (728 Hampton Rd) is hosting a fall festival. Special flavors and treats, music, vendors, face-painting, horse drawn wagon rides, and more.

Pomfret | Peg Loom Weaving Workshop | 2-4pm $ - Learn how to create your own kneeling pad/seat cushion/pet bed/decor/gift with Easy Acres Gnomestead (728 Hampton Rd). Tix

Putnam | Oktoberfest | 4pm - Bear Hands Brewing Company (75 Main St) is holding a German-themed evening. German music, food, contests/raffles, and of course, beer. BYO Stein, and dress up in lederhosen or a dirndl, if you’d like.

Scotland | Barn Bash | 7pm $ - I wouldn’t normally throw something like this in here, but since it’s in Scotland, and it involves live music, here we are. Help celebrate a 50th birthday, and jam out with live music at Hurricane Farm (65 Kasacek Rd). BYOB, $20 donation for music, and make sure to only park on one side of the road. Who knows? You might make some new friends!

Willimantic | BlOckoberFest | 2-6pm - The wonderful folks that bring you 3rd Thursday are bringing an Oktoberfest-themed party to Riverside Drive. 3,500sqft beer garden (featuring WilliBrew selections), brats and other German-themed food, live music, Bavarian pretzels, food trucks, vendors, pumpkin painting, and non-alcoholic drinks by Reframe: A Dry Spot. This looks like it will be an amazing time!

Willimantic | Glow in the Dark Yoga | 5:30-6:45pm $ - Get ready for yoga with a twist. YONO yoga (59 Church St) is turning on the blacklights and breaking out the glow in the dark paint for this unique yoga session. Tix

Willimantic | Exhibition Opening | 12pm $ - Contradictions Of Freedom Part II is opening at the Windham Textile and History Museum (411 Main St). If you’re interested in quiltmaking, this exhibition runs until early December.

Willimantic | Farmers Market | 8am-12pm - Get in your fresh produce and products at the Willimantic Farmers Market (28 Bridge St).

Willimantic | Royal Oaks: Unplugged | 8-10pm $ - Support local talent (they’re from Willimantic!) and a local business at this unplugged concert at The River Room (50 Riverside Dr). Come see the irreverent energy they bring that has earned them the title of “Connecticut’s silliest rock band.” More info and tix

Woodstock | German Car Autumn Classic | 12pm - Taylor Brooke Brewery (818 Rt 171) is hosting a celebration of German engineering, from vintage Volkswagens to modern Mercedes. Enthusiasts should make the trip and enjoy live music, beer, family-friendly activities. The best part? You’ll be supporting dachshund rescue efforts!

LIVE MUSIC

⬢ Riverside Park - Thompson | Wooden Horse | 1:30-3pm
⬢ Triple Raven Brewing | Tony Garcia | 4-7pm
⬢ Stomping Ground - Putnam | Briezy Jane and The Hurricane | 1-4pm
⬢ Broken Crust - Putnam | John Rodgers | 5:30-7:30pm

Ashford | NipMuck Marathon and Relay | 8am ($) - No, that’s not a typo. This NipMuck race has two options: take on the full 26.4 mile marathon on yourself, or split it up with another person. This is a race through the woods, so sticks, rocks, mud, and everything is all part of the package. Registration ends 10/2. Sign Up

Canterbury | 10th Anniversary Party | 11am-3pm ($) - Help celebrate 10 years of Russo’s Roots (289 N Society Rd). Food, music, farm tours, and pumpkin picking! There are two ticket options, one free - for people who are bringing their own food, and another option for those looking to eat the food provided by the farm. Tix

Dayville | Adoption Event | 10am-1pm - Paws Rescue League is holding an adoption event at the Dayville Petco (1086 Killingly Commons). If you want to take a puppy home on the same day, make sure you get pre-approved.

Oneco | Build a Scarecrow | 1pm - Angel & Anchor Farm (41 Newport Rd) is holding a free scarecrow building event. You bring the clothes, they provide the stuffing and twine. Make sure to say hi to Mac & Cheez, their mini donkeys!

Pomfret | Apple Cider Donut Festival | 12-2pm - Lapsley Orchard (403 Orchard Hill Rd) is holding an autumn experience with free apple cider donuts and apple cider! Take a hayride, and enter to win some door prizes. You can also bring your gently used coats to donate to “Button Up Connecticut.”

Putnam | Annual Road To Wellness | 10am-12pm $ - Hale YMCA is holding an morning of fitness-related events to help raise money for wellness programs, such as LIVESTRONG. More info

Windham | Tag/Vendor/Craft/Grinder Sale | 9am-2pm - The American Legion (339 Bricktop Rd) is squeezing in a lot in a little time. Do a little shopping and grab a grinder (contact Robin (860) 803-3014 to get your order in ahead of time). Vendors will be inside and outside.

Woodstock | Fall Into Books | 12-5pm - Taylor Brooke (818 Rt 171) is celebrating literary wonder, with a book fair, featuring numerous local authors. Adult books and children’s book will be available.

Woodstock | Wyndham Land Trust Ride Fundraiser | 9am $ - Spend the day riding the gorgeous landscape of the Wyndham Land Trust preserves. Questions? Visit their website or email Penny at [email protected].

LIVE MUSIC

⬢ Stomping Ground - Putnam | The Willie J Laws Band | 1-4pm
⬢ Stomping Ground - Putnam | Open Mic | 7pm

LIVE MUSIC

⬢ Music Lady Cafe - Central Village | Brandt Taylor Band | 5:30-7:30pm