Things to Do This Weekend: Apple Harvest Festival, Celebrate Wallingford
Southington's Apple Harvest Festival, Celebrate Wallingford, Guilford Porchfest, a chalk art festival and the first haunted nights of the season, Oct. 2–4.
Southington's 57th Apple Harvest Festival opens on the Town Green Friday evening, October 2, and Celebrate Wallingford fills downtown Wallingford with vendors, food and live music on Saturday and Sunday.
Guilford holds its third Porchfest on Saturday, with musicians playing from porches and lawns across downtown, and more than 60 artists work in chalk along New Haven's Broadway the same afternoon, while New Haven Pride takes over the corner of Orange and Crown streets. Twelve Percent Beer Project in North Haven holds its Oktoberfest on Saturday and Sunday. The region's haunted attractions open their seasons Friday night.
Southington's Apple Harvest Festival Opens the First of Two Weekends
The festival runs six days over two weekends and typically draws more than 100,000 people, according to the town, which organizes it. Admission, entertainment and parking at Southington High School are free. The carnival runs through all festival hours, and on Friday, the first of two Family Nights, a $30 wristband covers unlimited rides for the evening, the festival brochure shows. Food booths offer more than 80 items, with a dining tent at the top of Riccio Way.
Saturday's program includes an apple fritter eating contest for ages 7 and up, with sign-ups at the Information Booth that day, and fireworks at 8:30 p.m., launched from the Dog Park property on Mill Street. Sunday opens with the Southington Community YMCA's road races at 8:30 a.m.: a 5-mile race, a 5K, a 2-mile walk and fun runs. An apple pie eating contest for ages 16 and up follows at 12:30 p.m.
The parade steps off at 2 p.m. Sunday from Knowles Avenue and Summer Street in Plantsville and covers just over a mile to Eden Avenue. Victoria Triano is the grand marshal, and this year's theme is "Harvesting 250 years of American pride." The arts and crafts show, with more than 40 vendors, is on the second weekend only.
When: Friday, October 2, 5 to 9 p.m.; Saturday, October 3, 11 a.m. to 9 p.m.; Sunday, October 4, noon to 7 p.m. The festival returns October 9–11.
Where: The Town Green and surrounding streets, downtown Southington (75 Main St. for GPS)
Cost: Free. The Friday ride wristband is $30 per person.
Parking: Roads around the grounds, from High Street to Columbus Avenue, close an hour before opening each day, and on-street parking is prohibited. Free shuttle buses leave from Southington High School, 720 Pleasant St., on Saturday from 10:30 a.m. to 9:30 p.m. and on Sunday from 11:30 a.m. to 7:30 p.m.; there is no shuttle on Friday. Civic groups run paid lots around the center of town. On Sunday, parking is banned along the parade route from 7 a.m. to 10 p.m., and violators face a $35 fine or towing.
Rain dates: Fireworks, Saturday, October 10. Parade, Sunday, October 11.
Pets: Dogs and other pets are barred from the grounds by town ordinance; trained service animals are allowed.
Celebrate Wallingford Closes Center and North Main Streets
Wallingford Center Inc., the downtown business organization, runs the two-day street festival with vendors, food, live entertainment, children's activities and a "Happy Hour on Main" for those 21 and older. Entry is free. Dogs, skateboards and bikes are not allowed, according to the event flyer.
The Wallingford Police Department's road-closure notice, issued September 29, shuts South Main Street between Center and Prince streets starting at noon Friday. Center Street between Elm Street and Whittlesey Avenue, and North Main Street between Center and Church streets, close at 6 a.m. Saturday. The closures last until about 8 p.m. Sunday, and parking is prohibited on Center and North Main streets both days. On Sunday morning, the Fishbein/YMCA Community Road Race starts at about 9 a.m. from the YMCA's Eastside Branch at 81 South Elm St., closing parts of South Elm Street, South Main Street, Sylvan Avenue and Prince Street until about 11 a.m.
When: Saturday, October 3, 11 a.m. to 6 p.m.; Sunday, October 4, 11 a.m. to 5 p.m.
Where: North Main Street and Center Street, downtown Wallingford
Guilford Porchfest, in its third year and run entirely by volunteers, puts Guilford singers and musicians on porches, stoops, driveways, lawns and even barns throughout downtown for six hours on Saturday. Each performance is independently hosted. The organizers post the 2026 schedule, a street map and an online map on the festival's website.
When: Saturday, October 3, 11 a.m. to 5 p.m.
Where: Throughout downtown Guilford; maps on the festival's website
More Than 60 Chalk Artists on New Haven's Broadway
The Shops at Yale holds the 9th New Haven Chalk Art Festival on Saturday afternoon. More than 60 artists work to this year's theme, "Pop Culture Through Time," on Broadway Island at 56 Broadway, along a closed stretch of Elm Street and in Civil War Monument Park, and visitors vote for their favorites. The Family Fun Zone, in the courtyard behind 65 Broadway, has face painting, crafts and drawing lessons, and the first 200 children receive chalk at no cost. The Hitlist band plays near Broadway Island from 12:30 to 3:30 p.m.
When: Saturday, October 3, noon to 4 p.m. Rain date, Sunday, October 4.
Where: The Broadway District, New Haven
Cost: Free. Parking at the 150 York Street Garage is free from 11 a.m. to 6 p.m. with a validation stamp from The Shops at Yale tent on Broadway Island.
New Haven Pride Fills Orange and Crown Streets Saturday
The New Haven Pride Center holds New Haven Pride 2026 downtown on Saturday afternoon, during the same four hours as the chalk festival. The center's program lists live music and a DJ circle, drag performances and dancing, spoken word, larger-than-life puppets, a health and wellness village, and games for children and adults, with afterparties planned for the evening.
When: Saturday, October 3, noon to 4 p.m. Rain date, Sunday, October 4.
Where: The corner of Orange and Crown streets, downtown New Haven
Oktoberfest at Twelve Percent Beer Project in North Haven
Twelve Percent Beer Project calls its Oktoberfest "our biggest party of the year." The lineup at the State Street brewery includes dancers from HSV Bavaria, accordionist David Goclowski, the Grammy-nominated polka band Dennis Polosky & Maestro's Men, the Celtic folk group The Jolly Beggars and The Austrian Boys Band. The Meriden Turner Society and the Hop Häus food truck handle the food.
A day pass costs $20 and a weekend pass $30. Either includes an oversized Oktoberfest stein and a first pour each day, and weekend-pass holders are invited to a Friday night kickoff. Tickets are sold only to those 21 and older; anyone under 21 is admitted free with a parent or legal guardian.
When: Saturday, October 3, and Sunday, October 4. The event page does not list hours.
Where: Twelve Percent Beer Project, 341 State St., North Haven
A Pumpkin Trolley in East Haven and a Corn Maze in Guilford
The Shore Line Trolley Museum begins its Pumpkin Patch Trolley weekends on Saturday. Timed rides carry passengers to the museum's pumpkin patch, where each rider picks a sugar pumpkin to take home. The rides continue October 10, 11, 12, 17, 18, 24 and 25.
When: Saturday and Sunday, October 3–4, rides from 10:30 a.m. to 4 p.m.
Where: Shore Line Trolley Museum, 17 River St., East Haven
Cost: $17 adults, $15 seniors 62 and older, $13 children 2 to 18, plus fees
Bishop's Orchards' Fall Festival in Guilford is open daily through November 1 with a 4-acre corn maze and pick-your-own apples, pears, flowers and pumpkins. Wagon rides, a mega slide, an apple train, gem mining and food trucks run on weekends only.
When: Daily, 10 a.m. to 5 p.m.; the last ticket is sold at 4:30 p.m.
Where: Bishop's Main Orchard, 480 New England Road, Guilford
Cost: Weekend corn maze and activity area, $15 online or $18 at the gate; pick-your-own is extra
Four haunted attractions open on Friday, October 2, and each sells timed tickets in advance.
Trail of Terror, Wallingford: The volunteer-run outdoor trail at 60 N. Plains Highway is open Friday and Saturday, 7 to 11 p.m. Timed tickets are $28 and VIP passes $40, plus fees, and no tickets are sold at the gate. Parking at PNA Park is $10 per car, cash only. trailofterror.com
Nightmare's Gate, Northford: An outdoor walk-through of 11 scenes on the grounds of Cecarelli's Harrison Hill Farm, 1591 Middletown Ave., open from dusk to 11 p.m. Friday and Saturday and from dusk to 10 p.m. Sunday. Tickets start at $30; a "Not So Scary Haunt" starts at $20. nightmaresgatect.com
Haunt on Eden, Southington: A walk-through haunted house at Mount Southington Ski Area, 396 Mount Vernon Road, with entry at 7, 8 or 9 p.m. Friday and Saturday. Tickets are $27, parking included, and the haunt is recommended for ages 10 and up. hauntoneden.com
The Haunted Trolley, East Haven: "In Search of Sasquatch," a 30- to 45-minute interactive show aboard an antique trolley at the Shore Line Trolley Museum, with rides at 6, 7, 8 and 9 p.m. Friday and Saturday. Tickets are $29 in advance, and each ride holds 40 people. thehauntedtrolley.com
In Cheshire, the Cheshire Historical Society brings back its Spirits Alive! Cemetery Tour at Historic Hillside Cemetery on Friday and Saturday after a seven-year break, with costumed actors portraying eight figures from the town's history. The first tour leaves at 5 p.m. and the last at 8:15 p.m., and each takes about 1 hour and 45 minutes. Tickets are sold through the society's TicketSource page. cheshirehistory.org
New Haven: The New Haven Dragon Boat Festival puts paddling teams on the harbor Saturday from 7 a.m. to 4 p.m. at the Canal Dock Boathouse, 475 Long Wharf Drive. The organizer's tentative schedule starts the first heats at 8 a.m., the semifinals at 11:30 a.m. and the championship races at 2 p.m., with awards at 3:30 p.m.; free parking is nearby. canaldock.org
New Haven: Compassionfest, a day of vegan food, vendors and speakers, among them Gene Baur of Farm Sanctuary, is Sunday from 10 a.m. to 5 p.m. at Southern Connecticut State University's Moore Field House, 11 Wintergreen Ave. ctvegan.org
North Branford: Kent Falls Brewing's Northford taproom, 418 Forest Road, marks Oktoberfest on Sunday, open noon to 6 p.m., with Tim Palmieri playing from 2 to 4 p.m. kentfallsbrewing.com
West Haven: The city's 6th Annual Fire, Emergency Management, 911 ERS, Police & Health Expo is Saturday from 11 a.m. to 4 p.m. at Savin Rock Park, 6 Rock St., with a rain date of Sunday. Free. cityofwesthaven.com
Also nearby, Portland: The Portland Agricultural Fair runs Friday from 3 to 11 p.m., Saturday from 10:30 a.m. to 10 p.m. and Sunday from 10:30 a.m. to 6 p.m. at Chris Cote's Driving Range, 1401 Main St., across the Connecticut River from Middletown. Admission is $15 for adults, $10 for seniors 65 and older and active or reserve military, and free for children under 12. portlandfair.com
The festivals and haunted attractions post weather changes on their own websites, linked above.
