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Popular cities in Connecticut

Upcoming events in Connecticut

193 listed. Page 5 of 9

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Oct 1, 2026 Seymour, CT

Seymour Pumpkin Festival

Organizer Seymour Pumpkin Festival AssociationUnclaimed

The Seymour Pumpkin Festival is an organization with the purpose of providing a venue for local civic organizations and non-profits to raise funds while providing a wholesome form of family entertainment. All proceeds are to benefit community organizations. Get ready to celebrate a diamond milestone! The 60th Annual Seymour Pumpkin Festival is here, transforming French Memorial Park into a spectacular autumn wonderland bursting with color, creativity, and community pride. What began in 1965 as a modest harvest celebration organized by the Seymour Garden Club has grown into one of Connecticut’s most cherished fall traditions. Originally created to celebrate the season and raise funds for community beautification, the festival has blossomed into a regional favorite that draws thousands each year — all while keeping its warm, hometown charm. For six decades, this volunteer-powered event...

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Oct 1–31, 2026 Wethersfield, CT

Old Wethersfield Arts and Crafts Fair

Organizer VendorsMapUnclaimed

44th Annual Old Wethersfield Arts and Crafts Fair October 3, 2026 10:00 am - 4:00 pm - Wethersfield Historical Society Wethersfield Historical Society’s Tent will be filled with “ Attic Treasures” and treats. Our volunteer bakers will be offering delicious home-made goodies for sale. Throughout the year, our friends and neighbors have been donating one-of-a-kind items to our “Attic Treasures” that the society offers for sale to help support our educational programming. The Old Wethersfield Arts & Crafts Fair also welcomes other area non-profits like the Wethersfield Academy for the Arts, the Wethersfield Art League, and Ginger’s Jams and Jellies to share their work and missions with the community. Tickets are on sale now . Purchased in advance, tickets are $7 . At the gate on the day of the event, admission is $10. Tickets are available on EventBrite or save the ticketing fees and pur...

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Oct 2–4, 2026 Harwinton, CT

Harwinton Fair

Organizer Harwinton Agricultural SocietyUnclaimed

169th annual fair – Friday through Sunday – October 2nd, 3rd and 4th 2026 The Harwinton Agricultural Society is a nonprofit volunteer organization. Join us ! All of the exhibitors and volunteers for helping make the Harwinton Fair world famous. The Association of Connecticut Fairs, Inc. awards three (3) scholarships of $1,000.00 each to a graduating high school senior or a current college student to assist them with their education at an accredited institution of higher learning. Applications due by May 15th . The Harwinton Agricultural Society annual scholarships are available to all students who have worked or exhibited at the Harwinton Fair without discrimination as to race, color or creed. Applicants must be residents of Connecticut, and be enrolled at an accredited institution of higher learning. Previous recipients may also apply. Two scholarships of $1,500 each will be awarded...

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Oct 2–11, 2026 Southington, CT

Southington Apple Harvest Festival

Organizer Southington Apple Harvest Festival CommitteeUnclaimed

We are thrilled to announce the dates for the 2026 Southington Apple Harvest Festival ! Mark your calendars for one of the Northeast’s most iconic fall events! The Apple Harvest Festival returns for two exciting weekends of fun , flavor, and festivities drawing over 100,000 attendees to the vibrant Southington Town Green. The Southington Apple Harvest Festival is a six-day event that takes place over the course of two weekends each Fall. This annual eve nt is one of the largest and longest running festivals in the Northeast and typically draws a crowd of over 100,000 people. Interested in joining us for 2026? Vendor and participant applications will be available on our website in April or May . Stay tuned! In addition to this website, you can find the latest Festival information posted on Facebook , Twitter , and Instagram . Heads up, Southington! The JW Municipal Building lower parki...

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Oct 3–4, 2026 Old Saybrook, CT

Old Saybrook Arts & Crafts Festival

Organizer Greater Old Saybrook Chamber of CommerceUnclaimed

The 62nd Annual Old Saybrook Arts and Crafts Festival runs October 3 and 4, 2026, at 1 Main Street in Old Saybrook, Connecticut, with hours of 10 am to 5 pm Saturday and 10 am to 4 pm Sunday. More than 150 juried artists and crafters display work spanning ceramics, glasswork, jewelry, pottery, woodcraft and more.

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Oct 3–4, 2026 Windsor, CT

Windsor Fall Festival

Organizer VendorsMapUnclaimed

Brown's Harvest Fall Festival runs weekends from September 19 through November 1, 2026, plus Monday, October 12, from 10 am to 5 pm with final ticket sales at 4 pm. The farm event includes a 5 acre corn maze, a kids corn maze, hayrides, a barrel train, jump pad and chickens and turkeys to visit. A single day ticket costs $16.95 online or $18 at the door.

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Oct 3, 2026 Wethersfield, CT

Old Wethersfield Arts & Crafts Fair

Organizer Wethersfield Historical SocietyUnclaimed

The Old Wethersfield Arts & Crafts Fair returns to Cove Park with more than 90 juried artisans and vendors. Visitors can shop handmade art and gifts, see demonstrations, enjoy live music and food vendors, and browse the Historical Society's Attic Treasures and bake sale.

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Oct 10, 2026 Brooklyn, CT

Scotland Connecticut Highland Festival and Games

Organizer Highland Festival Association of Scotland CT Inc.Unclaimed

scotlandgames.org - Scotch Highland Festival & Games, Event, Bagpipes HOPE to see you on Saturday, October 10th, 2026. HOPE to see you on Saturday, October 10th, 2026. HOPE to see you on Saturday, October 10th, 2026. HOPE to see you on Saturday, October 10th, 2026. Just to remind everyone that we have moved our festival day to Saturday, October 10th, 2026 at the Brooklyn, Ct. Frgrnds During our regular November 2025 monthly meeting, discussion and a vote was taken to move our festival to a Saturday. This being said, our 2026 Highland festival & Games will be held it on Saturday, October 10, 2026. We hope that this will allow you to enjoy the day without having to rush from your church or other Sunday events going on.

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Oct 10–19, 2026 Gaylordsville, CT

Gaylordsville Columbus Day Arts and Fine Crafts Show

Organizer VendorsMapUnclaimed

39th Annual Columbus Day Weekend Arts & Fine Crafts Show Gala Preview Hors d'oeuvres, desserts, beverages, live music from Mama Train , a great band, and a chance to preview and purchase artwork, photography, fine crafts, jewelry, and glassware. Those looking for gifts of original artwork by local artists will find a great variety of framed oil paintings, watercolors and photography. The fall show also features the work of artisans in glass, jewelry, woodwork, pottery and more. Many local artists take advantage of the shows offered at the Hotel to sell their work and support the ongoing restoration of the building. A portion of all sales benefit the Hotel. Artists + Craftspeople , please be aware that once again, there are scammers on facebook and FairsandFestivals.net offering to sell you 'booth' space to show at our upcoming Arts & Fine Crafts Show. Our shows are juried, and you mus...

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Closed Sep 10, 2026

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Oct 10–11, 2026 Bethlehem, CT

Connecticut Garlic and Harvest Festival

Organizer VendorsMapUnclaimed

The 21st Annual Connecticut Garlic and Harvest Festival runs October 10 and 11, 2026, at the Bethlehem Fairgrounds, entrance at 304 Main St. North in Bethlehem. Hours are 9 am to 6 pm Saturday and 9 am to 5 pm Sunday, with garlic cooking demonstrations, growing lectures, a live band, specialty food vendors, a food court and pony rides. Admission is $10 for adults and $1 for children under 12, cash only.

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Oct 10–11, 2026 Windsor, CT

Brown’s Harvest Fall Festival

Organizer VendorsMapUnclaimed

Brown's Harvest Fall Festival brings classic autumn farm activities to Windsor, including hayrides, a five-acre corn maze, kids' maze, barrel train, jump pad, farm animals, pumpkins, and fall treats. The festival offers a family-friendly weekend destination with food and seasonal attractions.

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Oct 11–12, 2026 Stamford, CT

That's Amore Italian Festival Stamford

Organizer That's Amore FestivalUnclaimed

Mill River Park in downtown Stamford hosts That's Amore Italian Fest on October 11 and 12, from noon to 9 p.m., with free admission. Food vendors on hand include DeYulio's Sausage Company, Divina and Just Cannoli Bar, while live performers include Francesco Castiglione and Biagio on Saturday and Alessandro and Vittorio DiCarlo on Sunday.

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Oct 11–12, 2026 Bethlehem, CT

Connecticut Garlic & Harvest Festival

Organizer Connecticut Garlic & Harvest FestivalUnclaimed

The 21st Annual Connecticut Garlic and Harvest Festival runs October 10 and 11, 2026, at the Bethlehem Fairgrounds on Route 61, Saturday 9 am to 6 pm and Sunday 9 am to 5 pm. Shoppers can browse garlic and fall produce stands, sample garlic dips and cheeses, eat at a food court serving garlic sausage and garlic pizza, and take in cooking demonstrations and growing lectures. Admission is 10 dollars for adults and 1 dollar for children, cash only.

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Oct 16–18, 2026 Gaylordsville, CT

Gaylordsville Columbus Day Weekend Arts and Fine Crafts Show

Organizer VendorsMapUnclaimed

39th Annual Columbus Day Weekend Arts & Fine Crafts Show Gala Preview Hors d'oeuvres, desserts, beverages, live music from Mama Train , a great band, and a chance to preview and purchase artwork, photography, fine crafts, jewelry, and glassware. Those looking for gifts of original artwork by local artists will find a great variety of framed oil paintings, watercolors and photography. The fall show also features the work of artisans in glass, jewelry, woodwork, pottery and more. Many local artists take advantage of the shows offered at the Hotel to sell their work and support the ongoing restoration of the building. A portion of all sales benefit the Hotel. Artists + Craftspeople , please be aware that once again, there are scammers on facebook and FairsandFestivals.net offering to sell you 'booth' space to show at our upcoming Arts & Fine Crafts Show. Our shows are juried, and you mus...

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Closed Sep 10, 2026

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Oct 16–18, 2026 Glastonbury, CT

Glastonbury Apple Harvest & Music Festival

Organizer Glastonbury Chamber of CommerceUnclaimed

Join us for a weekend filled with music, food, and family fun in Glastonbury, CT, as we commemorate a half-century of unforgettable festivities. Our Award Winning Festival runs Friday, October 17 from 5 pm to 10 pm, Saturday, October 18 from 10 am to 10 pm and Sunday, October 19 from 11 am to 5 pm. Experience a vibrant array of activities: live music performances (50 bands on 4 stages), crafters showcasing their talents, to delicious food vendors serving delightful treats and thrilling carnival rides for all ages. 21+ are welcome to join us in our popular Harvest Pub featuring Sam Adams brews and Crystal Ridge wines. Enjoy an exciting schedule of live music that brings together local bands and renowned artists, making this festival a haven for music lovers. Dance, sing, and celebrate with us under the stars. Savor an eclectic variety of food vendors offering everything from traditiona...

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Oct 17–18, 2026 Simsbury, CT

Tower Toot

Organizer Friends of Heublein TowerUnclaimed

Did you know the creation of the Moscow Mule cocktail started with a Heublein? The Talcott Mountain State Park is open 365 days a year, from 8:00 AM until sunset. Open Friday, May 22 nd , 2026 and will close Monday, November 2 nd , 2026. The Tower is open Fridays, Saturdays, Sundays and Mondays during those months. Join The Friends of Heublein Tower for the beloved annual Tower Toot Festival, October 18–19! Enjoy peak foliage, scenic hiking, live music, hearty bites—all while supporting the preservation of the iconic Heublein Tower. A fall tradition not to miss!

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Oct 17–18, 2026 Woodstock, CT

Woodstock Fine Arts and Craft Festival

Organizer VendorsMapUnclaimed

First Congregational Church of Woodstock Fall Art and Craft Show 2026 at 543 Route 169 in Woodstock, CT will be held on Saturday, October 17 from 10am to 4pm and Sunday, October 18 from 11am to 4pm. In mid-October each year, we celebrate the New England Autumn and hold our annual Arts and Crafts Fair. Over 50 local artists and vendors exhibit and sell their art, jewelry, pottery, wood and metal crafts, fiber art, bird houses and much more! Saturday October 17 • 10AM - 4PM Sunday October 18 • 11AM - 4PM Footlong grilled Hotdogs Mac and Cheese Pulled Pork Sandwiches Mexican Street Corn Nachos and more! The event takes place rain or shine with vendors both inside and outside the church building.

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Nov 1–30, 2026 North Haven, CT

North Haven Holiday Welcome Craft Festival

Organizer VendorsMapUnclaimed

Wyndham Hotel, 1284 Strongtown Rd. (CT-188), Southbury, CT Space size 8' x 6' Hours 11 - 5 OPEN Fee: $100 Municipal Center (front lawn), 1 School St., Bethel, CT Space size 12' x 12' Hours 10 - 4 OPEN Fee: $75 Space size 12' x 12' Hours 11 - 4 OPEN Fee: $175 Municipal Center (front lawn), 1 School St., Bethel, CT

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Nov 6–8, 2026 Uncasville, CT

Uncasville Christmas Festival

Organizer New England Christmas FestivalUnclaimed

An award-winning food festival inside of an American-handmade-craft festival inside of a resort. Artisan Promotions presents the New England Christmas Festival! 300+ pop-up-shops of American made high-quality crafts and specialty foods. 3 Days Only Mohegan Sun in Connecticut.

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Nov 29 – Dec 21, 2026 New Haven, CT

Winterfair New Haven

Organizer WinterFairUnclaimed

Winterfair opens on the second level of New Haven Union Station's Great Hall for seven market days starting the first Saturday after Thanksgiving. This year it runs Saturdays and Sundays, 11 am to 4 pm, from November 28 through December 20, with more than 30 vendors each day and over 100 small businesses taking part overall.

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Nov 29 – Dec 21, 2026 Hartford, CT

Winterfair Hartford

Organizer WinterFairUnclaimed

Winterfair 2025 takes place inside Hartford Union Station’s Great Hall and will be home to over 30 vendors each of the eight market days starting the first weekend after Thanksgiving. 2026 will be our 6th anniversary! Over 100 small and micro local, diverse businesses are set to participate. Hartford’s Vendor Application is now closed. New Haven application still open here Want to avoid downtown traffic? Leave your car behind! Whether you’re coming from near or far, Winterfair is conveniently accessible with public transportation. Travel by train right into Hartford Union Station with CTrail Hartford Line or get dropped off right in front with CTfastrak or CTtransit. Want to visit Winterfair but downtown parking stresses you out? Don't worry, we are making it easy and offering discounted parking while you shop at Winterfair! If you park in the Spruce Street lot at 36 Spruce Street, Ha...

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Nov 29, 2026 Northford, CT

Holiday Artisan Market @ Millpond

Organizer Kim MuchaUnclaimed

Cindy Witter began 24 Peace to carry on the creativity of her late sister and artist, Linda Studley. Portfolios filled with Linda’s illustrations and Cindy’s unsurpassed giving nature, and the support of family and friends, drive this business forward and out into the community. Our motivation is to build a label representing products you can feel good about owning with a focus on product lines that are made from recycled, reusable, organic, and biodegradable materials. Our brand includes comfy, affordable & eco-friendly clothing, stationery, and stylish products. 24 Peace offers good-for-the Earth products that benefit great causes while helping to support unique art from a broad range of artists and offers something for everyone — with a spotlight on personal expression. What would happen if for 24 hours everyone in the world experienced peace? If for 24 hours nobody was killed, bul...

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Dec 1–31, 2026 Middletown, CT

Wadsworth Mansion Holiday Bazaar

Organizer Wadsworth Mansion at Long HillUnclaimed

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