Make your life happening by enrolling to entertainment events in Pittsfield. Find a partner through a salsa night or take your partner to live in concerts by upcoming bands in your town. Get high while playing Beer Pong in a pub crawl or attending stand-up comedy events in Pittsfield. Shake your legs in the happy streets, zumba or dance workshops or go for a film screening in the nearby cafes or theaters.
Explore Entertainment Events in Pittsfield.
## Entertainment Events in Pittsfield - **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 - **Date**: Fri Sep 25 2026 at 06:30 pm – Fri Sep 25 2026 at 10:00 pm (-04:00) - **Event URL**: https://allevents.in/pittsfield/dolly-drag-party/100002000080799512 - **Venue**: Dottie's Coffee Lounge - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEwL2Jhbm5lcnMvNWEwNzA3NDczZmNhNjYzODhmODEwZTY3ZDAzMjU1ZmUxNDJlYTI0YzhlNzczMDQyMGZhMTE2M2U3NjRlOGQxNC1yaW1nLXcxMDgwLWgxMzUwLWRjZjhmOGY4LWdtaXIuanBnP3Y9MTc4ODgzMDE2Mw.avif - **Price**: USD 13 - **Categories**: parties, entertainment - **Event Name**: Deadgrass - **Description**: A string band jamgrass adventure through Jerry Garcia’s musical world Step into a rootsy, free-spirited journey through the music of Jerry Garcia with Deadgrass, a jamgrass string band led by Matt Turk and C Lanzbom. Joined by bassist Dave Richards, banjo - **Interested Audience**: - Count: 13 - **Date**: Fri Oct 09 2026 at 07:30 pm (-04:00) - **Event URL**: https://allevents.in/pittsfield/deadgrass/200030395837834 - **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/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czMvYmFubmVycy83NTM5OGU2MTgxNzhjZDYyMWZmMjZhYzE2YmZmYWQxNTU0MDJkN2IyYjYxZmRjMzg5ZDlkZmJiMmZmODg3MDEzLXJpbWctdzEyMDAtaDYyOC1kYzE4MDgwOC1nbWlyP3Y9MTc4ODAyMDQxMg.avif - **Categories**: music, entertainment, concerts, live-music, art, fine-arts, trips-adventures - **Event Name**: Yesterday and Today: The Interactive Beatles Experience - **Description**: Step into the excitement of the British Invasion with Yesterday and Today: The Interactive Beatles Experience, a nostalgic journey through the music that changed everything. Created by brothers Billy, Matthew and Ryan McGuigan, this isn’t a typical tribut - **Interested Audience**: - Count: 21 - **Date**: Fri Oct 16 2026 at 07:30 pm (-04:00) - **Event URL**: https://allevents.in/pittsfield/yesterday-and-today-the-interactive-beatles-experience/200030427855431 - **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/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy9iODFmOTUzZjFjZjVlNTczODk0Yzg4Nzk0MTkzYjQyMThjYWNjODcxMzVmZWY2NTE5YWUwMTM4YmUwZDI1MmRlLXJpbWctdzEyMDAtaDYyOC1kYzc4MjgxOC1nbWlyP3Y9MTc4ODAyMDQwNg.avif - **Categories**: music, entertainment, concerts, art - **Event Name**: The Boy Band Project - **Description**: Throw it back to the golden age of pop with The Boy Band Project, a high-energy concert that captures the heart of late-’90s and early-2000s boy band mania. Think TRL countdowns, bedroom posters and choreographed moves you memorized after school. With Bro - **Interested Audience**: - Count: 7 - **Date**: Sat Oct 17 2026 at 07:30 pm (-04:00) - **Event URL**: https://allevents.in/pittsfield/the-boy-band-project/200030439024711 - **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/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEwL2Jhbm5lcnMvNTNiZDZjYzU0YjMyOWJjZmUwYjZiMDdjYjBkODEwYTk2MTkxYWIxNGJhODVjYjNlMzEzNmNjZmNjMWNhMzg0Yy1yaW1nLXcxMjAwLWg2MjgtZGMwODE4MjgtZ21pcj92PTE3ODc0NDMwMzA.avif - **Categories**: entertainment, music, concerts, performances - **Event Name**: The Polar Express with Santa Claus - **Description**: 'Tis the Season! Join us at Phoenix Theatres for a magical holiday event that will fill your heart with joy! On Saturday, December 12th, Santa Claus is taking a special detour from the North Pole to make a jolly appearance at our theatre! Phoenix Theatr - **Interested Audience**: - Count: 48 - **Date**: Sat Dec 12 2026 at 10:00 am – Sat Dec 12 2026 at 02:00 pm (-05:00) - **Event URL**: https://allevents.in/pittsfield/the-polar-express-with-santa-claus/200030546068237 - **Venue**: 57 North St, Pittsfield, MA, United States, Massachusetts 01201 - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czMvYmFubmVycy9mZjkwN2QyODAyYjBjMDRmN2I5M2QxMWYxMjRhZmM2NDZlY2E5NmZmNDBjYmIxYjdkZGQ4ZGUxNzY4YTc3NmEwLXJpbWctdzgyMC1oMzEyLWRjZTgyODQ4LWdtaXI_dj0xNzg4NDgwOTQx.avif - **Categories**: art, theatre, christmas, holiday - **Event Name**: Aquanett LIVE at Proprietor's Lodge - **Description**: Aquanett returns to The Proprietors Lodge this fall! If you love 80s Rock / Metal this is a show you don't want to miss! A great night of LIVE music! Come early for dinner before the show! Pub style menu - 5:00pm Call the venue for reservations at - (41 - **Date**: Sat Nov 21 2026 at 08:00 pm (-05:00) - **Event URL**: https://allevents.in/pittsfield/aquanett-live-at-proprietors-lodge/200030709268434 - **Venue**: The Proprietor's Lodge - Lakefront Events, Dining & Venue - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEvYmFubmVycy9jOWQ0YjQ2MjhlNGRkZDFlN2QyNTQ4MjExYmNjZGFjZGFlMTkyMDlhM2Y1NzVmZDNhZmU0ZWIxYmVlYzk2ODE4LXJpbWctdzEyMDAtaDc5OS1kYzA4MDgwOC1nbWlyP3Y9MTc4OTYyMjczNA.avif - **Categories**: Music, Entertainment, Concerts, Workshops - **Event Name**: Candlelight: A Haunted Evening of Halloween Classics - **Description**: "Candlelight: A Haunted Evening of Halloween Classics tickets 🎟️ Experience the thrill of live entertainment with Candlelight: A Haunted Evening of Halloween Classics! Whether it's a night out with friends or a moment you've waited for, this is your ti - **Interested Audience**: - Count: 1 - **Date**: Fri Oct 30 2026 at 07:00 pm (-04:00) - **Event URL**: https://allevents.in/pittsfield/candlelight-a-haunted-evening-of-halloween-classics/200030678761952 - **Venue**: South Congregational Church - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czQvYmFubmVycy8wNjlmNzRiN2ZiZjk4OGZmMDNlMDIxYjlkMzFjNjFmYTg5YzI2OWNhMWQyZGMyNzAyZjRkOTExNmNkNzgwODdlLXJpbWctdzEyMDAtaDc5OC1kYzA4MDgwOC1nbWlyP3Y9MTc4ODk0MjI5Mg.avif - **Categories**: candlelight-concerts, halloween - **Event Name**: The Polar Express for $1 - **Description**: All aboard! Phoenix Theatres is proud to bring back our annual $1 showings of The Polar Express, starting December 11th! Gather the whole family for this magical holiday tradition on the big screen in 100% heated reclining seats. Don’t miss your chance to - **Interested Audience**: - Count: 98 - **Date**: Fri Dec 11 2026 at 10:00 am – Wed Dec 16 2026 at 02:30 pm (-05:00) - **Event URL**: https://allevents.in/pittsfield/the-polar-express-for-$1/200030510697310 - **Venue**: 57 North St, Pittsfield, MA, United States, Massachusetts 01201 - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czEvYmFubmVycy9jNDAwMGMwYzU3OTNiNDE2MGQyMmQ2YmEyMTc2OWZiOWQzMjY0YTA4M2M2MjMwZjVjZjllOWMyY2NhY2Y0Nzk5LXJpbWctdzEyMDAtaDYwMC1kYzE4Mzg1OC1nbWlyP3Y9MTc4ODU4NDc2Ng.avif - **Categories**: art, theatre, holiday - **Event Name**: New Years Eve Party POLISH FALCONS Pittsfield - **Description**: Rock the night away with HB Funk and the Horns Band. Appetizers, Dinner, Cash Bar, Champagne toast at midnight & Midnight Munchies. Now taking Reservations - Party starts at 5:30PM - **Interested Audience**: - Count: 32 - **Date**: Thu Dec 31 2026 at 05:30 pm (-05:00) - **Event URL**: https://allevents.in/pittsfield/new-years-eve-party-polish-falcons-pittsfield/200030709271043 - **Venue**: Polish Falcons of America Nest 580 - **Banner**: https://dyn-image.allevents.in/generate-image?v=4&title=New+Years+Eve+Party+POLISH+FALCONS+Pittsfield+&date=Thu+Dec+31+2026+at+05%3A30+pm&bg=4 - **Categories**: new-year, entertainment, parties, music - **Event Name**: The Little Mermen & The Princess Pals: Disney Sing Along - **Date**: Sat Nov 21 2026 at 02:00 pm – Sat Nov 21 2026 at 04:00 pm (-05:00) - **Event URL**: https://allevents.in/pittsfield/the-little-mermen-and-the-princess-pals-disney-sing-along/2300030376516811 - **Venue**: Colonial Theatre - Pittsfield - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czQvYmFubmVycy84MTZiZmFhMC1iNTI5LTExZjEtODczNS03NzNjNWRkZWRiNDgtcmltZy13MTIwMC1oMTIwMC1kY2Y4ZjhmOC1nbWlyLmpwZz92PTE3ODk5MzI1Mjk.avif ## 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**: The States in Between Tour - **Description**: Shannon Tehya and Keegan James are continuing their “States in Between” tour with an intimate listening room concert.About this EventShannon Tehya and Keegan James are continuing their “States in Between” tour with an int - **Venue**: WANDER Berkshires - **Banner**: https://cdn-az.allevents.in/events7/banners/e2a2d59f8f995d597df943a04050541281e0e81929c96d9c0e539964c8246922-rimg-w1200-h1500-dcf8d8c8-gmir.jpg?v=1788361229 ## Browse Entertainment Events by Date - [Entertainment Events Today in Pittsfield](https://allevents.in/pittsfield/entertainment--today) - [Entertainment Events This Weekend in Pittsfield](https://allevents.in/pittsfield/entertainment--this-weekend) - [Entertainment Events in September in Pittsfield](https://allevents.in/pittsfield/entertainment--september) - [Entertainment Events in October in Pittsfield](https://allevents.in/pittsfield/entertainment--october) ## FAQs - **Q**: What are the top Entertainment events in Pittsfield? - **A:** Dolly Drag Party (Fri Sep 25 2026 at 06:30 pm at Dottie's Coffee Lounge), Deadgrass (Fri Oct 09 2026 at 07:30 pm at The Colonial Theatre - 111 South St., Pittsfield, MA, United States, Massachusetts 01201), Yesterday and Today: The Interactive Beatles Experience (Fri Oct 16 2026 at 07:30 pm at The Colonial Theatre - 111 South St., Pittsfield, MA, United States, Massachusetts 01201), The Boy Band Project (Sat Oct 17 2026 at 07:30 pm at The Colonial Theatre - 111 South St., Pittsfield, MA, United States, Massachusetts 01201), The Polar Express with Santa Claus (Sat Dec 12 2026 at 10:00 am at 57 North St, Pittsfield, MA, United States, Massachusetts 01201). - **Q**: What Entertainment events are happening in Pittsfield this weekend September 25–27, 2026? - **A:** Dolly Drag Party (Fri Sep 25 2026 at 06:30 pm at Dottie's Coffee Lounge), Dolly Drag Party (Fri, 25 Sep at 06:30 pm at Dottie's Coffee Lounge). - **Q**: What Entertainment events are happening in Pittsfield in September 2026? - **A:** Dolly Drag Party (Fri Sep 25 2026 at 06:30 pm at Dottie's Coffee Lounge), Dolly Drag Party (Fri, 25 Sep at 06:30 pm at Dottie's Coffee Lounge). - **Q**: How can I find Entertainment events in Pittsfield? - **A:** You can discover upcoming Entertainment 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 Entertainment 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 Entertainment events in Pittsfield? - **A:** Some popular venues hosting Entertainment events in Pittsfield include Dottie's Coffee Lounge, The Colonial Theatre - 111 South St., Pittsfield, MA, United States, Massachusetts 01201, 57 North St, Pittsfield, MA, United States, Massachusetts 01201. - **Q**: What is the price range for Entertainment events in Pittsfield? - **A:** Prices for Entertainment events in Pittsfield range from USD 13 to USD 13. Many events also offer free entry. - **Q**: Who are the top organizers for Entertainment events in Pittsfield? - **A:** Popular organizers hosting Entertainment events in Pittsfield include jess rufo, Berkshire Theatre Group, Phoenix Theatres Beacon Cinema. - **Q**: Are there any online Entertainment events available? - **A:** Yes, many Entertainment 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 Entertainment events in Pittsfield? - **A:** Follow the Entertainment category on AllEvents.in to get notified when new Entertainment events are listed in Pittsfield. ## Category Banner - **Banner Image**: https://cdn2.allevents.in/transup/58/5efbefdb8e438db5c829e697673309/Maskgroup-3-.webp ## Entertainment events from nearby cities - [Entertainment events in Dalton](https://allevents.in/dalton-ma/entertainment) - [Entertainment events in Lenox](https://allevents.in/lenox-ma/entertainment) - [Entertainment events in West Stockbridge](https://allevents.in/west-stockbridge/entertainment) - [Entertainment events in Stockbridge](https://allevents.in/stockbridge-ma/entertainment)