Witness the crazy comedy shows 2026 in Pittsfield at the venues near you to laugh till your belly hurts. You cannot miss the chance to witness the popular names of the comedy scene. There are improv workshops, comedy class and comedy shows in Pittsfield too where you can try your hands out.
Lighten yourself and laugh it out at a stand up comedy event happening near you in Pittsfield.
## Comedy Events in Pittsfield - **Event Name**: Vanya - **Description**: October 8-24 Mark H. Dold stars in this one-man adaptation of Chekhov’s classic tale of love, art, and attempted murder. Comedic and tragic, our shared humanity is thrust into sharp focus in Vanya. This fresh adaptation explores the kaleidoscope of human - **Date**: Fri Oct 09 2026 at 07:30 pm – Fri Oct 09 2026 at 09:00 pm (-04:00) - **Event URL**: https://allevents.in/pittsfield/vanya/200030394317201 - **Venue**: 30 Union St, Pittsfield, MA, United States, Massachusetts 01201 - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czMvYmFubmVycy9lOTE1YjY1ZDcwY2U4ZDM3ZWEwY2Q0YjdlNmQyNmUyYWNiMjIzMjQzOWE3YzUwODA2YThjYmRlMzNiNmMxMzRlLXJpbWctdzEwODAtaDE1MDItZGMxODE4MTgtZ21pcj92PTE3ODgzMDE5MTY.avif - **Categories**: art, theatre, comedy, entertainment - **Event Name**: David Sedaris - **Date**: Thu Oct 01 2026 at 07:30 pm – Thu Oct 01 2026 at 09:30 pm (-04:00) - **Event URL**: https://allevents.in/pittsfield/david-sedaris/2300030365113527 - **Venue**: Colonial Theatre - Pittsfield - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czIvYmFubmVycy9hZDM5NTYxMC1iMjgwLTExZjEtYTFlMy04ZGJhNjY0ZDE1ODctcmltZy13MTA4MC1oMTA4MC1kYzk4Njg1OC1nbWlyLmpwZz92PTE3ODk2NDAxNDU.avif - **Event Name**: Yes Darling - **Description**: With Ryan Montbleau and Hayley Jane Yes Darling is a musical comedy about two artists whose greatest performances happen both onstage and behind closed doors. Part concert, part theatrical comedy and part hilariously candid exploration of modern relation - **Date**: Fri Nov 13 2026 at 07:30 pm (-05:00) - **Event URL**: https://allevents.in/pittsfield/yes-darling/200030709268133 - **Venue**: The Colonial Theatre - 111 South St., Pittsfield, MA, United States, Massachusetts 01201 - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czkvYmFubmVycy9lYzZjZmJmMzQ3MTY2YzNlYzIxYzJiNzBlN2I5OTQxY2ExNThiZWQ0ZDdjOGJhMmZiYmMyOTYwNjhmNGJjNGNlLXJpbWctdzEyMDAtaDYyOC1kY2M4YzhjOC1nbWlyP3Y9MTc4OTYyMjczMQ.avif - **Categories**: comedy, Entertainment, Music, Concerts ## Trending Events in Pittsfield - **Event Name**: Local Love Arts Festival & Berkshires Jazz Summer Showcase - **Description**: The inaugural Local Love Arts Festival will take place on Sunday, September 27, 2026, from 10:00 am to 3:00 pm at The Common in Downtown Pittsfield. Local artists will take center stage — showcasing their work, connecting with new audiences, and reminding - **Venue**: The Common Park - **Banner**: https://cdn-az.allevents.in/events8/banners/421a198fee199e81fb43ae92b14dd5738df110555da19e1433af4511c10a5830-rimg-w1200-h552-dc480828-gmir?v=1789461857 - **Event Name**: Dolly Drag Party - **Description**: Join us for a spacial night of drag, drinks and dolly as Dottie's collars with Haus of Jewels, the biggest drag house in the Berkshires.About this EventThis will be a night to remember! Expect 6 performances iaccross 2 ro - **Venue**: Dottie's Coffee Lounge - **Banner**: https://cdn-az.allevents.in/events10/banners/5a0707473fca66388f810e67d03255fe142ea24c8e7730420fa1163e764e8d14-rimg-w1080-h1350-dcf8f8f8-gmir.jpg?v=1788830163 - **Event Name**: The Ultimate Cher Experience - **Description**: Snap out of it and turn back time with The Ultimate Cher Experience—a dazzling, high-energy tribute celebrating the one and only Cher. Featuring Lisa Carter, this spectacular show captures the voice, attitude and larger-than-life glamour that made Cher a - **Venue**: The Colonial Theatre - 111 South St., Pittsfield, MA, United States, Massachusetts 01201 - **Banner**: https://cdn-az.allevents.in/events9/banners/911f73388ff549524be5636d5e329602c5ad2cc015ccfe4b0abd56544b7cff01-rimg-w1200-h628-dcc8d8e8-gmir?v=1787443032 - **Event Name**: Rev Tor's Anniversary Jam - **Venue**: Colonial Theatre - Pittsfield - **Banner**: https://cdn-az.allevents.in/events1/banners/6d445350-b4e9-11f1-8735-773c5ddedb48-rimg-w1200-h675-dc080808-gmir.jpg?v=1789905007 - **Event Name**: Free Robotics Workshop For Kids at Pittsfield, MA (7-14yrs) - **Description**: Searching for the best robotics classes for kids in Pittsfield, MA?Register for the Moonpreneur complimentary in-person workshop and transform your child's curiosity into creation. After our previous event got completely booked, we - **Venue**: Holiday Inn & Suites Pittsfield-Berkshires by IHG - **Banner**: https://cdn2.allevents.in/thumbs/thumb6ab0bbed97fe5.jpg - **Event Name**: FULL MOON MAZE MADNESS - **Description**: What is better than a FULL MOON? A FULL MOON CORN MAZE! Join us for a LIGHTS OUT, FULL MOON MAZE This maze is not designed to scare our guests, if you want to be scared visit us during our Haunted Maze! Navigate the maze with the moon light only! W - **Venue**: 384 Webster Mills Road , Pittsfield, NH, United States, New Hampshire 03263 - **Event Name**: Candlelight: Tribute to Adele - **Description**: "Candlelight: Tribute to Adele tickets 🎟️ Experience the thrill of live entertainment with Candlelight: Tribute to Adele! Whether it's a night out with friends or a moment you've waited for, this is your time to be part of something special. Find ti - **Venue**: South Congregational Church - **Banner**: https://cdn-az.allevents.in/events7/banners/7f64f6558de259175b434cd08b53651c23d92708c9472f8bf18206b4dbaeb6cd-rimg-w1200-h531-dc080808-gmir?v=1788301917 - **Event Name**: Harvest Run and Community Fun - **Description**: Join us for Harvest Run & Community Fun on Saturday, Sept. 26, at Berkshire Community College! Enjoy a 5K trail run, the return of the free Kids 1-Mile Fun Run, a health and wellness fair, family activities, seasonal treats, a cook-off with Integritus - **Venue**: Paterson Field House - **Banner**: https://cdn-az.allevents.in/events10/banners/62b692ccea2f1776c61dafc43957b85caf8dbbc1f4ab52adade24bf51a508a32-rimg-w1200-h628-dcf8f8e8-gmir?v=1788584766 - **Event Name**: Toys For Tots Annual Musical Bingo Fundraiser - **Description**: It’s almost time for Toys For Tots Annual Musical Bingo Event! 🎶 Buy your tickets/save your spot ahead of time/reserve tables, by contacting Bridget Keegan. 🎟️🎶 Phone: 413-464-1616. 📱 VENMO:Bridget-Keegan-1 💸 Tickets: $25/pp (2 bingo cards/6 games total - **Venue**: Berkshire Hills Country Club - **Banner**: https://cdn-az.allevents.in/events9/banners/f2857f6c3a6b0a288458f71c0b02eb79e6afcdc3838c1f1dc5d04ab17e37306e-rimg-w942-h2048-dc080808-gmir?v=1787758239 ## Browse Comedy Events by Date - [Comedy Events Today in Pittsfield](https://allevents.in/pittsfield/comedy--today) - [Comedy Events This Weekend in Pittsfield](https://allevents.in/pittsfield/comedy--this-weekend) - [Comedy Events in September in Pittsfield](https://allevents.in/pittsfield/comedy--september) - [Comedy Events in October in Pittsfield](https://allevents.in/pittsfield/comedy--october) ## FAQs - **Q**: What are the top Comedy events in Pittsfield? - **A:** Vanya (Fri Oct 09 2026 at 07:30 pm at 30 Union St, Pittsfield, MA, United States, Massachusetts 01201), David Sedaris (Thu Oct 01 2026 at 07:30 pm at Colonial Theatre - Pittsfield), Yes Darling (Fri Nov 13 2026 at 07:30 pm at The Colonial Theatre - 111 South St., Pittsfield, MA, United States, Massachusetts 01201). - **Q**: How can I find Comedy events in Pittsfield? - **A:** You can discover upcoming Comedy events in Pittsfield on AllEvents.in. Browse by date, venue, or price to find events that match your interests. - **Q**: How do I buy tickets for Comedy events in Pittsfield? - **A:** You can buy tickets directly through AllEvents.in. Many events offer online booking with options for free, paid, and early-bird tickets. - **Q**: What are the popular venues for Comedy events in Pittsfield? - **A:** Some popular venues hosting Comedy events in Pittsfield include 30 Union St, Pittsfield, MA, United States, Massachusetts 01201, Colonial Theatre - Pittsfield, The Colonial Theatre - 111 South St., Pittsfield, MA, United States, Massachusetts 01201. - **Q**: Who are the top organizers for Comedy events in Pittsfield? - **A:** Popular organizers hosting Comedy events in Pittsfield include Barrington Stage Company, Ticket Network Events, Berkshire Theatre Group. - **Q**: Are there any online Comedy events available? - **A:** Yes, many Comedy events are available online. You can filter for virtual events on AllEvents.in to attend from anywhere. - **Q**: How can I get notified about new Comedy events in Pittsfield? - **A:** Follow the Comedy category on AllEvents.in to get notified when new Comedy events are listed in Pittsfield. ## Category Banner - **Banner Image**: https://cdn2.allevents.in/transup/f3/0e051f4d9a4429ae6be27084e31353/comedy.png ## Comedy events from nearby cities - [Comedy events in Dalton](https://allevents.in/dalton-ma/comedy) - [Comedy events in New Lebanon](https://allevents.in/new-lebanon-ny/comedy) - [Comedy events in West Stockbridge](https://allevents.in/west-stockbridge/comedy) - [Comedy events in Stockbridge](https://allevents.in/stockbridge-ma/comedy)