You can make the most of a January week in Connecticut when you know where to look. Cold weather narrows the options, but it also brings focused events, smaller crowds, and better access to shows, food festivals, and indoor attractions across the state.
Here’s a quick guide to worthwhile events happening across Connecticut from January 18–24, 2026, so you can plan your time without too much guesswork. You’ll find a mix of live music, comedy, theater, food gatherings, and some practical travel tips to help you move between them with fewer surprises.
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1) Attend Cypress Hill live at Westville Music Bowl, museums/new-haven-museum-in-new-haven-connecticut/”>New Haven
Cypress Hill brings their tour to New Haven at the open-air Westville Music Bowl, just outside downtown. The venue keeps crowds manageable compared to bigger spots.
Westville Music Bowl gives you good sightlines and decent sound from most seats, but if you’re in the lawn area, expect to stand for a while. Weather can be a wildcard—shows go on rain or shine, and there’s not much cover, so dress for the forecast.
Cypress Hill’s lineup usually features a full band with a set focused on their classics. To check dates and tickets, see the Cypress Hill tour schedule or the Bandsintown listing for Westville Music Bowl.
Parking fills up fast. Arrive early if you can. Rideshares work, but after the show, you might find yourself waiting out the traffic on Yale Avenue.
2) See Rob Thomas perform in Connecticut
Rob Thomas is playing in Connecticut this week—a solid pick if you want a familiar, low-key concert. He’s bringing solo work and Matchbox Twenty favorites to Bridgeport, a city he calls a “home show.” Local coverage confirms it: Rob Thomas performing in Bridgeport.
The show’s at the Hartford HealthCare Amphitheater, an outdoor venue near the harbor. Sightlines and sound are good, but January nights get chilly. Bundle up. Parking can be a headache, so plan extra time.
If you want to double-check before buying tickets, look up his official concert dates and ticket details. That way, you can see if this date or another works better.
3) Enjoy Jose Feliciano’s concert this week
Spend an evening this week catching José Feliciano live in Connecticut. He tours regularly, and his Northeast stops always seem to draw a mix of longtime fans and people seeing him for the first time.
Expect Latin pop, soft rock, and acoustic arrangements. The vibe is relaxed—great if you prefer a seated show with clear sound instead of a high-energy crowd. He’s polished and professional, not flashy.
Before heading out, check dates and venues on the José Feliciano tour schedule. Listings update often, which matters in winter.
For last-minute tickets or alerts, peek at José Feliciano concert dates on Bandsintown. Smaller spots may sell out, but bigger halls sometimes release seats close to showtime.
Winter traffic and weather can be unpredictable, so leave yourself some wiggle room, especially if you’re driving from outside Hartford or New Haven.
4) Visit the Middletown Food Truck Festival
You might want to plan ahead for the Middletown Food Truck Festival, a popular annual event with local trucks, live music, and family activities. The festival usually runs midday to evening, with free admission and parking—easy on the wallet.
There’s a wide range of food, from comfort classics to regional stuff. Lines build up during peak hours, so going early helps you try more vendors.
Heads up: this festival doesn’t usually happen in January. Dates shift each year, so check the official Middletown Food Truck Festival listing before making plans.
If you’re into outdoor dining and community vibes, keep this one in mind for a warmer Connecticut visit.
5) Explore New Britain’s Food Truck Festival
If you’re thinking ahead to later in the year, put the New Britain Food Truck Festival on your list. It’s usually held at New Britain Bees Stadium and brings in a ton of regional food trucks.
According to the New Britain Food Truck Festival listing, this festival happens in August—not January. So, it won’t be running during the January 18–24 window.
When it’s in season, expect outdoor dining, long lines at peak times, and limited seating. It’s perfect if you like sampling lots of small bites.
If you’re a food truck fan, the Connecticut food truck festival calendar helps you track events all year. Handy if New Britain’s dates don’t match your trip.
6) Experience the Bishop’s Orchards Peach Festival
Bishop’s Orchards Peach Festival is a mid-August thing, not a January event. So if you’re in Connecticut this week, you’ll have to wait for this one.
When it does run, the Peach Festival in Guilford is all about peak peach season. You get live music, food trucks, cider, and family activities across the orchard. It’s laid-back but can get crowded by mid-morning.
Arrive early and keep your plans flexible. Parking goes fast, lines form at the best vendors, and it’s more about atmosphere than a packed schedule. If you want a quieter farm day, visiting Bishop’s Orchards on a regular weekday might suit you better.
The farm market, winery, and seasonal picking are open year-round, so you can still make a stop—even if peaches aren’t in season.
7) Watch comedian Julian McCullough at Mohegan Sun Casino
Julian McCullough is live at Mohegan Sun Casino this week, performing at Comix Roadhouse. It’s a smaller venue, so you’re close to the stage and the pace stays snappy.
McCullough’s style is conversational, shaped by years on the road and TV. If you follow stand-up, you might’ve seen him on late-night shows or big tours. His material covers everyday stuff, not shock humor, so it’s easy for most folks to enjoy.
Catch show details and times on the Julian McCullough at Mohegan Sun event page.
Comix Roadhouse is just off the casino floor, so expect crowds and parking delays, especially on weekends. You can check seating and food options on the Comix Roadhouse comedy club calendar.
8) Catch R&B Only Live at Toyota Oakdale Theater
Spend a night at R&B Only Live at the Toyota Oakdale Theatre in Wallingford. The show runs through R&B hits from the ‘90s to today, with no openers or long breaks.
The Dome (as locals call it) offers assigned seats and clear views, though parking can drag on busy nights. If you want comfort over standing in a crowd, this is a good midwinter concert pick.
R&B Only Live draws a mixed crowd—older fans and younger listeners alike. People are into the music but not rowdy, so it’s a chill vibe.
Plan ahead for bag rules and possible lines at security. Event info and tickets are on the official R&B Only Live Wallingford page.
It fits nicely into a weekend if you want live music without straying far from central Connecticut.
9) See The Lion in Winter play this week
Catch The Lion in Winter at a local theater this week for some sharp dialogue and family power struggles—classic drama, not spectacle.
Most venues are small, so you’re close to the action. Productions might not be flashy, but you get a personal, focused experience.
Check dates and locations on a reliable Connecticut events calendar. January schedules can change last minute, especially with weather.
Arrive early for parking and seating; ushers often juggle a bunch of roles. If you’re after a calm, meaningful indoor night out, this play’s a solid bet.
10) Attend Dinosaur World Live event
Dinosaur World Live stops in Connecticut theaters this January as part of its U.S. tour. The show uses big puppets and simple stories to introduce prehistoric animals—great for kids, but adults usually find something to enjoy too.
Want more details? The Dinosaur World Live in Connecticut listing covers the basics and age range. The show moves at a steady pace, which keeps younger kids engaged, though teens might find it a bit simple.
Multiple venues host performances, including New Haven, New London, and Torrington. For times and seats, check the Shubert Theatre New Haven Dinosaur World Live page.
It’s a short show with limited concessions—easy to fit into an afternoon. Parking and accessibility depend on the theater, so look up details before you buy tickets.
Connecticut Travel Tips for January
Traveling in Connecticut in January means dealing with cold and shorter days. A little planning goes a long way—smart packing and realistic transportation plans will help you stay comfortable and on schedule.
Weather and Packing Recommendations
Daytime temps usually run 25–40°F, colder at night inland. Coastal spots like New Haven and Mystic are a bit milder, but wind off Long Island Sound can cut right through you. Snow comes and goes, and icy sidewalks are pretty common after storms.
Bring insulated boots with good grip—slush and refrozen snow pile up near curbs and parking lots. You’ll want a midweight coat, hat, and gloves for days with lots of walking.
Layering’s key. Museums, casinos, and restaurants crank the heat, so a thermal base and a zip-up sweater let you adjust. Toss in a small umbrella—winter here is more about light snow or chilly rain than blizzards.
Transportation and Getting Around
Give yourself extra time for travel, especially in the mornings. Overnight freezing can make roads slick, even if things look clear. Highways get plowed fast, but side roads lag behind.
If you’re renting a car, ask for all-season tires and make sure the washer fluid won’t freeze. Parking garages help in cities like Hartford and New Haven.
Public transit is best along the coast. Metro-North Railroad runs reliably from New Haven to NYC, even in bad weather. Local buses cover the state, but weekend schedules get thin.
Rideshares are around, but waits get longer during storms. Walking is fine in downtowns, though sidewalks can be icy or uneven after snow.
Making the Most of Local Events
Connecticut serves up a steady mix of winter festivals, comedy, museum programs, and food events this week. Locals know where to look for listings and how ticketing works at different venues—worth keeping in mind to save yourself some time and hassle.
Where to Find Community Gatherings
Honestly, you’ll get a clearer sense of what’s actually happening if you check statewide or regional calendars instead of just scrolling through social feeds. Sites like best things to do this weekend in Connecticut stick to up-to-date listings—think pop-up markets, tastings, quirky seasonal stuff.
For ticketed happenings, I usually poke around platforms that round up smaller venues. The Connecticut events on Eventbrite page pulls in local workshops, live music, and neighborhood fundraisers you might not spot anywhere else.
If you’re more into classic attractions, take a look at curated guides like top things to do in Connecticut. You’ll find museums, historic spots, and plenty of indoor picks—especially handy when it’s freezing outside.
Navigating Ticketing and Reservations
Check ticket requirements early—weekend events fill up fast. Comedy shows, brewery tastings, and guided tours? They’ll often sell out by midweek, even in the dead of January. The CTvisit upcoming events calendar lists pricing, age restrictions, and whether you need to buy ahead.
Look at the venue details before you buy. Smaller theaters or event rooms might only offer will-call, have limited seating, or just a cash bar. Parking can be all over the map, too.
Here’s a quick checklist before you lock in your plans:
- Start times: lots of winter events kick off earlier than you’d think.
- Refund policies: double-check them, especially with the weather flipping on a dime.
- Location: some listings use a nearby town instead of the exact spot—easy to miss.
Paying attention to these details can save you a headache later.
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