Discover events, food and drink specials, activities, and limited-time promotions in Cheshire, CT. Explore what's happening today and what's coming up.

Events, Deals and Things to Do in Cheshire, CT

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Cheshire, CT

Record Store Release Parties

Counter Weight Brewing Co. Oktoberfest

Oktoberfest

Sin Barreras Online Playwriting Forum (Oct 3)

Sin Barreras Online Playwriting Forum (Oct 19)

Eli's Garden of Healing Makers Market

Muse Holiday Market

Best Trivia Ever

Can't-Miss Events, Deals and Experiences

Trivia Night (Tuesdays)

$1 Wings (Tuesdays)

Burger Night

Family Pizza Night

Family Pizza Night (Thursdays)

Music Bingo (Thursdays)

Famous Names Trivia (Thursdays)

Trending Events, Deals and Experiences

Virtual Auction

Upcoming Events, Deals and Experiences

Have you heard about the Acorns & Oaks Parent & Child Class at the LA Arboretum? This Autumn, families and little ones are invited to gather under the oaks to enjoy the wonders of nature! The class features delightful activities like singing apple tales, observing playful squirrels, and enjoying the crisp fall mornings. Sunday mornings will be filled with an autumn-inspired circle time, unique family crafting, and the stunning beauty of the garden, complete with the incredible peacocks. It's a perfect way to connect with nature and each other in a playful setting. Registration is now open, so be sure to check out the details and enroll through the link in the bio of @laarboretum! Check the link below for more information.

Acorns & Oaks at LA Arboretum Parent & Child Class

Get ready for the world's largest pro-am pole dancing competition coming to Los Angeles! The 2026 PSO Pacific & After Dark Pole Championships will showcase incredible talent across various categories including Championship, Dramatic, DTF (Down to Flow), Doubles/Groups, Entertainment, Hard Style, Showcase, and Showstopper. Competitors will be divided into levels from Amateur 1-4 to Professional Level 5, with top performers in each category earning a chance to advance to the 2027 Nationals. Age groups will include Junior, Senior, Master, and Grand Master, ensuring a diverse range of participants. Don't miss out on this exciting event where artistry and athleticism collide! For those interested in competing, the registration deadline is July 19. Tickets will be available soon, so stay tuned for updates!

2026 PSO Pacific & After Dark Pole Championships

You'll love this opportunity to escape the heat and immerse yourself in nature! Join a ranger for a guided hike at Bluff Lake Reserve, where you can explore the stunning scenery surrounded by lush greenery and tall trees. This tranquil setting is perfect for those looking to connect with the outdoors. Space is limited, so make sure to register in advance as reservations are required. Participants must be ages 16 and older, and all attendees will need to complete a liability waiver upon arrival. Don't miss out on this chance to enjoy a beautiful hike in the mountains!

Guided Hike: Explore Bluff Lake

You have to check out the upcoming Cars / Coffee event at Garage 79! This vibrant gathering features a stunning lineup of classic and modern cars, all set against the picturesque backdrop of a rustic red building and lush greenery. It's the perfect opportunity to connect with fellow car enthusiasts, showcase your ride, and enjoy the lively atmosphere. Make sure to mark your calendars for this exciting event happening every third Sunday. Bring your friends, grab a coffee, and soak in the automotive culture. For any inquiries or to share your excitement, feel free to reach out via email!

GARAGE 79 CARS / COFFEE

Just discovered this delightful Sunday Breakfast at San Pedro Elks Lodge! It's the perfect way to unwind and enjoy a delicious meal with loved ones. The menu is packed with mouthwatering options like fluffy pancakes, Belgian waffles, hearty omelets, breakfast burritos, chilaquiles, and steak & eggs. Whether you're starting your day with family or catching up with friends, this breakfast spread is sure to please everyone. The atmosphere is bright and inviting, making it a great spot to relax and savor your morning. Elks members and their guests are welcome, so come hungry and make this Sunday breakfast a cherished tradition! Check the link below for more information.

Sunday Breakfast

Check out the U-Pick Berries event at The Corral at SLO Ranch! This fun activity is available on weekends, allowing you to pick your own fresh berries right from the farm. It's a great way to enjoy the outdoors and connect with nature. While you're there, don't miss out on other exciting activities like pony rides, hay rides, and feeding the farm animals. The atmosphere is lively and inviting, perfect for families and friends looking to make lasting memories. For more information, feel free to reach out via email!

U-Pick Berries

This weekend at Fox Point Farms, you can hop on a tractor for a fun and informative tour of the farm! The tractor tours are scheduled for Saturday and Sunday, running every 30 minutes from 9 AM to 6 PM, with the last tour at 4 PM and 6 PM. It's a great opportunity to explore the beautiful surroundings and learn about the farm's operations. Whether you're with family or friends, this experience promises to be enjoyable and educational. Don't forget to check out the Harvest Market and other activities happening throughout the day. For reservations, email info@foxpointfarms.com.

Tractor Tours (Sep 19–20)

This caught my eye! If you're looking for a refreshing way to enjoy your Sunday, check out Mimosa Sundays at Route 66 Classic Grill. For just $3, you can sip on delicious mimosas all day long. The elegant champagne flutes filled with vibrant orange mimosa cocktails are perfect for a cheerful celebration. Surrounded by bright yellow mimosa flowers, the atmosphere is both fresh and inviting. It's the ideal way to relax and refresh your weekend!

Mimosa Sundays

Mimosa

This looks like the ultimate spot for Ravens fans! Scoozzi's is hosting the Ravens Game Day Live, a lively watch party every Sunday. With an electrifying atmosphere featuring DJ Tony Clay, you won't want to miss the excitement. The venue is decked out in vibrant purple, gold, and silver, creating a dynamic setting perfect for cheering on your team. Gather your friends and enjoy the game with fellow fans in a fun and energetic environment. Make sure to mark your calendars and get ready for an unforgettable football experience!

Ravens Game Day Live

Bring your friends to enjoy a delightful Sunday Brunch at The Grill, starting at 9am. Indulge in a variety of delicious starters, sandwiches, and main dishes. The Grill is open daily with breakfast, lunch, and bar services. Don't miss out on this all-day brunch experience! Check the link below for more information.

Sunday Brunch

Can't wait for this amazing happy hour at Dog Haus! They have a fantastic menu featuring sliders with cheese and caramelized onions, plus some delicious saucy chicken wings served with a dipping sauce. Don't forget to try their Cocktail of the Month, the Watermelon Cooler, made with watermelon vodka, lemon, agave, and pineapple juice. It's the perfect way to wrap up your weekend with family and friends. The inviting bar atmosphere, complete with a wooden counter and a backdrop of liquor bottles, makes it a great spot to relax and enjoy the day. Whether you're dining in, taking out, or getting delivery, this happy hour is a must-try!

Dog Haus Happy Hour — All Day Sunday

I just found out about the Sunday Brunch at the Club, and it sounds amazing! Every Sunday, they offer a delightful brunch experience that you won't want to miss. The atmosphere is set against a stunning desert landscape, perfect for a relaxing meal. Whether you're looking to enjoy a leisurely morning with friends or a family gathering, this brunch is the ideal way to unwind. Plus, the club has a variety of delicious options to choose from, ensuring there's something for everyone. For any questions or reservations, you can reach out via email.

Brunch (Sundays)

You'll love the Sunday Side Quest at O'Shaughnessy Distilling Co.! This weekly event invites you to gather your friends and dive into a world of board games, from classics like Clue and Scrabble to competitive strategy games. Enjoy a cozy atmosphere with big tables that allow you to spread out and play without any elbowing. Indulge in delicious snacks like $5 chips and dip, perfect for game time, and sip on the $10 Keeper's punch or choose from a full menu of craft cocktails. Plus, catch football on the big screen while you play. Bring your favorite games or pick from the extensive collection available. No cover charge means you can focus on fun and bragging rights!

Sunday Side Quest

Plus a full menu of craft cocktails to choose from.

Keeper's punch

The ultimate game-table snack. Plus a full menu of distillery bites to share.

chips & dip

Have you heard about ASSSSCAT at UCB LA? This is a fantastic improv comedy show that takes place every Saturday and Sunday, bringing together some of the best comedic talent in the city. The atmosphere is cozy and inviting, perfect for a night of laughter with friends. The show features a group of talented performers who create hilarious scenes based on audience suggestions, ensuring that no two shows are ever the same. It's a great way to discover the next big comedy star while enjoying a fun night out. Don't forget to grab your tickets linked in the bio!

ASSSSCAT

Just discovered this exciting NFL event at Mic's West Hollywood! They're kicking off every Sunday at 9:30 AM to catch the 10 AM game kickoff, making it the perfect spot for football fans. Enjoy happy hour from opening until 6 PM, featuring free bar snacks and delicious food options from Irv's Burgers and Ggiata. Don't miss out on their Red Zone shot specials and a variety of Bloody Mary and margarita options. Plus, there's never a cover charge, so you can enjoy the games without any hassle. This place is all about good vibes and great company, making it your new favorite local hangout!

NFL IS BACK

entry

bar snacks

You have to check out the Record Store Release Parties happening to celebrate Beck's new album, Ride Lonesome! This is a fantastic opportunity to gather with fellow music lovers and enjoy the album together. The event features exciting prizes and giveaways, making it a fun experience for everyone involved. Participating record stores across various states will be hosting these release parties, so find the one nearest to you and join in on the celebration. Don't miss your chance to be part of this musical gathering and enjoy some great company while listening to new tunes!

September 18 at 6PM at Redscroll Records. Prizes, giveaways, gifts with purchase while supplies last.

Beck Release Party

You should check out the 9th Annual Oktoberfest Celebration at Counter Weight Brewing Co.! This three-day event promises a traditional German experience filled with beer, food, games, and entertainment. Kick off the festivities on Friday with StichfaB Tappings starting at 3 PM, delicious food specials from Ritual Pizza Co., and fun activities like Underberg Bingo. Saturday features a lively Bavarian Folk Dance, live screen printing, and a Stein Hoisting Competition, along with more German-inspired food. Don't miss Family Day on Sunday with traditional music, face painting, and more competitions. It's a fantastic way to gather friends and family for a weekend of fun!

Had to post about this amazing Oktoberfest event at Counter Weight Brewing Co.! It's a three-day celebration featuring a fantastic lineup of German-inspired beers, including Fest Bier Lager, Workhorse Pilsner, Ein Helles Lager, Dunkel Lager, Marzen Lager, and Drudenhaus Rauchbier, all available for draft pours and from traditional Stichfaß vessels. The atmosphere will be lively with authentic food, entertainment, and games to enjoy throughout the weekend. Plus, entry is free! This is the perfect opportunity to gather with friends and celebrate the spirit of Oktoberfest with great brews and fun activities.

So excited about the Sin Barreras Online Playwriting Forum! This event is hosted by Melanie Queponds and is part of the Latine Heritage Month celebrations. It's a fantastic opportunity for aspiring playwrights to explore their creativity and connect with others in the community. The forum will take place on October 3rd, and it's designed to empower participants through storytelling. Don't miss out on this chance to engage with fellow writers and enhance your skills in a supportive environment. For more information, feel free to reach out via email.

This looks like an amazing opportunity to dive into the world of playwriting! The 'Sin Barreras Online Playwriting Forum' is hosted by Melanie Queponds and is part of the Latine Heritage Month celebrations. This forum is designed to empower voices and stories from the Latine community, providing a platform for creative expression. It's happening on October 19th, and it's a great chance to connect with fellow writers and explore the art of storytelling. Don't miss out on this enriching experience that honors our roots and heritage through the power of narrative. For more information, you can reach out via email.

You should check out Eli's Garden of Healing Makers Market! They're currently seeking vendors for this exciting event happening on a Saturday. With roughly 10 vendor spaces left, it's the perfect opportunity for artisans to showcase their work. This year's market is set to host double the vendor capacity and has extended hours, plus food trucks will be on site! If you're interested in becoming a vendor, make sure to get your applications in ASAP. For more information, you can reach out via email. This is an event you won't want to miss!

Had to post about the Muse Holiday Market happening this November! It's a fantastic opportunity for local vendors to join in and create a vibrant shopping experience filled with community spirit, gift-giving, and holiday cheer. This year marks the 3rd annual market at Muse Coworking Collective, and they're inviting all local creators and small businesses to apply. Each vendor will receive a marketing kit, a spotlight feature, and inclusion in the Holiday Gift Guide leading up to the event. Applications are open until October 15, so if you have products perfect for the holiday wishlist, don't miss out on this chance to showcase them! The market will take place on Saturday, November 21, from 10 AM to 3 PM. It's a great way to support local and find unique gifts for the season!

You'll love this trivia night at Mezzo Grille! Every Thursday at 7 PM, gather your smartest friends for a fun-filled evening of trivia that covers everything from pop culture to sports and music. The atmosphere is vibrant and playful, making it the perfect spot to show off your knowledge. Plus, the first-place team wins a Mezzo gift card, and there are new prizes every week! It's a great way to unwind, enjoy some cocktails, and prove you know way too much about absolutely nothing. Don't miss out on the excitement and camaraderie of trivia nights that truly don't suck!

Can't Miss

Check out Trivia Night at Terrace on the Green every Tuesday at 6 PM! This event features new themed rounds each week, making it a fresh and exciting experience every time. Gather your friends and compete for prizes awarded to the top three teams, plus enjoy the bragging rights that come with victory! It's a fun-filled evening perfect for everyone, whether you're a trivia master or just looking for a good time. Don't forget to come hungry, as you can also enjoy $1 wings while you play. Make it a part of your weekly routine and enjoy a night of laughter and friendly competition!

wings

Just discovered this amazing $1 Wings promotion at Terrace on the Green! Every Tuesday, you can indulge in delicious glazed chicken wings, perfectly garnished with herbs and onions. The atmosphere is inviting, with a beautiful outdoor setting that enhances your dining experience. Plus, after enjoying your wings, you can stick around for Trivia Night, where new themed rounds are presented each week, and prizes await the top three teams. It's a perfect way to enjoy a fun evening with friends while savoring some tasty wings!

Can't wait for Burger Night at Do What Thou Wilt Pizza Co! Every Wednesday night, they’re serving up delicious single patty smashburgers and special burgers that are sure to satisfy your cravings. The smashburgers are just $6, and the special burgers are $7, both without fries. Plus, enjoy $2 off Headway IPA and Workhorse Pilsner draft pours to wash it all down. The atmosphere is casual and inviting, perfect for a midweek treat. Don't forget to join in on the fun with Mix Tape Match Music Bingo hosted by @digitaltracksdj starting at 6:30 PM. It's a great way to enjoy good food, drinks, and some friendly competition!

Single Patty Smash Burgers

Single Patty Special Burgers

Headway IPA & Workhorse Pilsner Draft Pours

Had to post about this awesome Family Pizza Night happening every Thursday! You can enjoy delicious personal size pies for just $9, or go for the classic cheese and margherita pies at $13. Plus, there's $2 off on Headway IPA and Workhorse Pilsner draft pours to wash it all down. It's a perfect night for families to gather and enjoy some great food together. Don't forget to join in on the fun with Trivia Night hosted by @barratedent at 6:30pm. It's a casual and inviting atmosphere, making it a great way to spend your Thursday evening with loved ones.

Personal Size Pies

Cheese & Margherita Pies

Had to share this awesome Family Pizza Night happening every Thursday! You can enjoy delicious cheese and margherita pies for just $13, or grab a personal pie for only $9. Plus, there's a fantastic deal on drinks with $2 off Headway IPA and Workhorse Pils pours. To make the night even more fun, trivia is hosted by @barratedent at 6:30 PM, so gather your family and friends for a night of great food and friendly competition. Don't miss out on this perfect way to kick back and enjoy some quality time together!

Personal Pies

Headway IPA & Workhorse Pils pours

Can't wait for Music Bingo at Terrace on the Green! This lively event combines your favorite songs with the classic game of bingo, creating a fun and interactive experience every Thursday. Starting September 17 at 6 PM, gather your friends and enjoy a night filled with music, laughter, and friendly competition. The atmosphere is vibrant, with musical notes and vinyl records adding to the festive decor. Don't miss out on the chance to win prizes while enjoying great food and drinks in a fantastic setting!

Had to post about this awesome trivia night! It's called Famous Names Trivia and it's happening every Thursday. Think you’re smart? Put your trivia knowledge to the test with a challenging 30-question quiz that’s free to play and open to everyone. The themed trivia promises quick rounds and big bragging rights, so gather your friends and see how you stack up on the leaderboard, which gets updated after grading. This is a perfect way to enjoy a fun night out while flexing your brainpower!

Famous Names Trivia

The Virtual Auction is part of the Mountainfilm on Tour event, which has been a cherished gathering for the community for over a decade. This year, the auction runs from September 11 through September 21, providing a unique opportunity for everyone to participate and support the Ojai Valley Land Conservancy (OVLC). The auction features a variety of items and experiences that reflect the spirit of adventure and conservation. Alongside the auction, attendees can enjoy award-winning short films, live music, and delicious food from local food trucks during the main event on September 19. This is not just an auction; it's a chance to connect with the community and contribute to a meaningful cause. Don't miss out on this opportunity to bid on exciting items while supporting the preservation of the beautiful Ojai Valley. Check the link below for more information.

Upcoming

Top Picks

Gotta make plans for Karaoke at Terrace on the Green every Friday! Starting September 18, this lively event kicks off at 6 PM, inviting everyone to grab the mic and showcase their singing talents. The atmosphere is perfect for a fun night out with friends, surrounded by a beautifully lit outdoor terrace and a vibrant crowd. Whether you're a seasoned performer or just want to cheer on your friends, this is the place to be. Don't forget to come for dinner and make it a complete evening of entertainment! For any inquiries, feel free to reach out via email.

Discover what's happeningin Cheshire, CTDiscover what's happening in Cheshire, CT

Featured

Record Store Release Parties

Trending

Record Store Release Parties

Oktoberfest

Counter Weight Brewing Co. Oktoberfest

Trivia Night (Tuesdays)

$1 Wings (Tuesdays)

Burger Night

Family Pizza Night

Family Pizza Night (Thursdays)

Music Bingo (Thursdays)

Famous Names Trivia (Thursdays)

Oktoberfest

Oktoberfest

Counter Weight Brewing Co. Oktoberfest

Upcoming

Virtual Auction

Record Store Release Parties

Oktoberfest

Counter Weight Brewing Co. Oktoberfest

Trivia Night (Tuesdays)

$1 Wings (Tuesdays)

Burger Night

Family Pizza Night

Family Pizza Night (Thursdays)

Music Bingo (Thursdays)

Top Picks

Virtual Auction

New

Karaoke (Fridays)

Muse Holiday Market

Famous Names Trivia (Thursdays)

Family Pizza Night

Oktoberfest

Sin Barreras Online Playwriting Forum (Oct 19)

Trivia Night (Tuesdays)

Burger Night

Music Bingo (Thursdays)

Sin Barreras Online Playwriting Forum (Oct 3)

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