The holiday season starts early around here this year. Over the next 10 days in Milford, Orange and West Haven: Dockside’s Christmas kickoff with Santa and the Grinch, live axolotls at the Orange library, a week of West Haven restaurant deals and First Church’s Homemade Holiday Fair. Here’s the lineup, day by day, checked against each organizer’s own listing.
Thursday, Nov. 12
- Yuletide at Dockside: Christmas Kickoff Party, Dockside Brewery, 40 Bridgeport Ave. It’s the debut of two new holiday rooms, the Gingerbread House and the Dockside Express, along with new decor, holiday cocktails and a seasonal menu. Santa and the Grinch visit from 5 to 8 p.m. More on Dockside’s kickoff.
- Why Choose a Community College? 6:30 to 7:30 p.m., Milford Public Library, 57 New Haven Ave. Bernard Shea, an admissions veteran with CT State Community College, talks with high school students in grades 9 to 12 and their parents or caregivers about the community college route. No registration.
- Virtual Author Talk: Chef Pyet DeSpain (Orange), 2 to 3 p.m., online through Case Memorial Library, 176 Tyler City Road. The first winner of Gordon Ramsay’s “Next Level Chef” talks about her cookbook, “Rooted in Fire: A Celebration of Native American and Mexican Cooking.” Register through the library for the link.
- Auditions for “American Buffalo,” 7 p.m., MAC Downtown, 40 Railroad Ave. South. Thursday is the second and last audition night for David Mamet’s play, which has roles for three men. Richard Mancini directs, and the show runs Feb. 5-20, 2027.
Saturday, Nov. 14
- All About Axolotls (Orange), 3 to 4 p.m., Meeting Room, Case Memorial Library, 176 Tyler City Road. Ashley from the Amphibian and Reptile Center brings live axolotls and covers their care, fun facts and science. For kids in kindergarten through grade 6; registration required.
- Arlington National Cemetery: An Historical Overview, 2 to 3 p.m., Milford Public Library, 57 New Haven Ave. A talk for adults, three days after Veterans Day. No registration.
- Literary Open Mic, 4 to 6 p.m., MAC Downtown, 40 Railroad Ave. South Read your own writing from the MAC stage to a supportive audience. Sign up online through the MAC.
Sunday, Nov. 15
- West Haven Restaurant Week begins and runs through Saturday, Nov. 21. Nineteen restaurants are offering prix-fixe menus and deals, from $1 Blue Point oysters at Moby Dick’s happy hour to a $49 dinner at The Breakwall. See every restaurant and its special.
- Dan Watson Live, 2 to 5 p.m., Dockside Brewery, 40 Bridgeport Ave. Afternoon live music on the water.
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Monday, Nov. 16
- Free AI Essentials certification class (West Haven) begins at the West Haven Community Center, 255 Meloy Road, and runs 10:30 a.m. to 1:30 p.m. Monday through Thursday. It’s free for West Haven residents. Here’s how to sign up.
Wednesday, Nov. 18
- Jurassic Classroom: Dinos 2 U (West Haven), 5:30 to 6:30 p.m., Connie Sacco Room, West Haven Public Library, 300 Elm St. Kids 3 to 12 can touch casts of real dinosaur fossils, make a dino craft, adopt a stuffed dinosaur to take home (while supplies last) and pose with an inflatable dinosaur. Drop in; no registration.
- Medicare Finances & More (West Haven), 5:30 to 6:30 p.m., first floor, West Haven Public Library, 300 Elm St. Stop by any time in that hour to talk with a representative. No registration.
- Fall Film: “Black Bag” (Orange), 1 to 2:30 p.m., Case Memorial Library, 176 Tyler City Road An afternoon spy thriller for adults (1 hr. 33 min.). Registration required.
- Laugh Tracks Standup Comedy with Christian Finnegan, 8 p.m. (doors 7:30), MAC Downtown, 40 Railroad Ave. South Finnegan was one of the original panelists on VH1’s “Best Week Ever” and played Chad in the “Mad Real World” sketch on “Chappelle’s Show.” Tickets through the MAC.
Friday, Nov. 20
- Homemade Holiday Fair presale night, 6 to 8 p.m., Fellowship Hall, First United Church of Christ, 34 West Main St. The $10 admission includes a soup supper, a piece of homemade pie and first dibs on fair items. There’s also a pie-making challenge. Tickets are sold at the door.
- Songbird: Halley Neal Sings Fleetwood Mac, 7:30 p.m., MAC Downtown, 40 Railroad Ave. South The Berklee-trained singer’s one-woman show covers Fleetwood Mac songs, from “Landslide” and “Songbird” to “The Chain” and “Dreams.”
Saturday, Nov. 21
- Homemade Holiday Fair, 10 a.m. to 3 p.m., First United Church of Christ, 34 West Main St. Admission is free. There’s a craft fair, photos with Santa, raffle prizes, a craft class, a nativity exhibit in the church, crafts for kids and holiday sweets. The church says the Saturday sea glass workshop is a separate ticket.
- Prognosis: The American Pink Floyd (Orange), doors 6:30 p.m., show 7:30 p.m., High Plains Auditorium, 525 Orange Center Road. A full set of Pink Floyd songs from every era plus music from “The Wall,” with a laser light show and a 30-foot wall built on stage. Seating is general admission by section; tickets are sold online.
- Teen Book Bedazzling (Orange), 2 to 4 p.m., Case Memorial Library, 176 Tyler City Road Teens in grades 7 to 12 bring a hardcover or paperback and cover it in diamond-art gems. Registration required.
Looking ahead: Thanksgiving week
- Food2Kids charity night at Dockside, Monday, Nov. 23, 5 to 7 p.m., 40 Bridgeport Ave. Dockside’s brewers made a special charity beer, and proceeds from every one sold during the event go to Milford Food2Kids.
- 6th Annual Milford Turkey Trot, 9 a.m. Thanksgiving morning, Thursday, Nov. 26. New this year: the race starts, finishes and celebrates at the Milford Academy and Natatorium soccer fields, 80 Park Circle, at the southeast corner of Gulf Street and New Haven Avenue. Register on the race’s RaceEntry page.
- Rotary Club of Orange Thanksgiving Turkey Trot, Thursday, Nov. 26, High Plains Community Center, 525 Orange Center Road. The 5K starts at 8 a.m. and the 1-mile walk at 8:05 a.m., rain or shine.
- Small Business Saturday in downtown Milford is Nov. 28, 10 a.m. to 3 p.m., and West Haven lights the tree on the Green at 4:30 p.m. the same day. Our downtown holiday guide has the rest of the season’s dates.
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