# Festivals in Westport, MA | Cultural Events & Fairs

- **Subtitle**: Explore upcoming festivals in  Westport, Massachusetts. Discover cultural celebrations, street fairs and seasonal events happening across the city. Join the festivities.
- **Category**: Festivals
- **Type**: category

## Audience

- **Followers**: 2.5M+
- **Recent Followers**: 
  - **Avatar 1**: https://cdn-az.allevents.in/events4/banners/c7a3bd77620a92a1fee77ed0b46cc305d65fcaf166695040aabebd480d9323a4-rimg-w200-h200-dc7e887a-gmir?v=1749580804
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## Featured Events

- **Event Name**: Hugo The Ultimate Journey Tribute Concert - One night only at CT Food Truck Battles Festival
  - **Description**: The music of Journey from Hugo The Ultimate Journey Tribute Band.  Covered general admission seats and VIP seat tickets are on sale.  Gates open at 12pm for the Food Truck Festival and gates open to the Hugo Concert at
  - **Date**: Sat, 16 May at 07:00 pm – Sat, 16 May at 08:00 pm (-05:00)
  - **Event URL**: https://allevents.in/wolcott/hugo-the-ultimate-journey-tribute-concert-one-night-only-at-ct-food-truck-battles-festival/80002385228519
  - **Venue**: Woodtick Recreation Area
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:600:300/g:sm/sh:100/aHR0cHM6Ly9jZG4yLmFsbGV2ZW50cy5pbi90aHVtYnMvdGh1bWI2OTYwYmZkOTE3ZWExLmpwZw.avif
  - **Price**: min: 39.19, max: 39.19, currency: USD
  - **Categories**: concerts, performances, music, entertainment, festivals, food-drinks, food-truck-festivals

## About

The best things to do in the world include attending top-notch festivals in [CITY]. Be it a rocking music festival or scrumptious food festival in [CITY], you will have a gala time of your life with a few of your close friends or your family. With the best of fun, entertainment, and food, the experience in festivals lets the enthusiasts immerse in the local culture and vibe. Ranging from the biggest outdoor beach parties to crazy music festivals, the festivals fall under various categories to suit everybody’s tastes. If you are looking for the best events and festivals in [CITY] listed on one platform - we have you covered.

Immerse yourself in the mega dance festivals, electrifying music festivals, theatre & film festivals, quirky local festivals and more with us!

## Festivals Events in Westport

- **Event Name**: 2026 Wine, Cheese & Chocolate Festival
  - **Description**: Join us on June 13, 2026, for an unforgettable day filled with the region's finest flavors at the Wine, Cheese & Chocolate Festival! 

Hosted by the Coastal Wine Group, this exceptional event lets you 
taste over 50 wines from 14 different vineyards,
  - **Interested Audience**:
    - Count: 1743
  - **Date**: Sat Jun 13 2026 at 11:00 am (-04:00)
  - **Event URL**: https://allevents.in/westport/2026-wine-cheese-and-chocolate-festival/200029711629338
  - **Venue**: Westport Fair Inc
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czkvYmFubmVycy8zMmMyYjNiM2U3NzhmZDY4NDhlYTg4ZmM2ZjRhODdhZjA4ODhmYTdjYWJlOGFkMzAwNzY1NjM0ZWEzZGZkZDNhLXJpbWctdzEyMDAtaDY2My1kY2Q3ZGJkZC1nbWlyP3Y9MTc3NDM4OTM3Ng.avif
  - **Categories**: wine-tasting, festivals
- **Event Name**: South Coast Harvest Festival 2026
  - **Description**: Your favorite New England fall festival is returning to the iconic Westport Fairgrounds! Mark your calendars for the 4th annual South Coast Harvest Festival- the ultimate family fall experience! Explore stunning professional garden displays by local lands
  - **Interested Audience**:
    - Count: 4852
  - **Date**: Fri Sep 25 2026 at 03:00 pm – Sun Sep 27 2026 at 06:00 pm (-04:00)
  - **Event URL**: https://allevents.in/westport/south-coast-harvest-festival-2026/200029687965259
  - **Venue**: South Coast Harvest Festival
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czIvYmFubmVycy8yODYyODAxMTcxMmMzY2NjZWQ1ODE3YTBlNGY2ZTgzODExNzc0MTBlZjE0OTc2OTNlODQ3MTg2MmYyYjQ3ODRmLXJpbWctdzEyMDAtaDE1MDAtZGM0ZTZkNGEtZ21pcj92PTE3NzUyMzc2Mzc.avif
  - **Categories**: festivals, harvest-festival, art, calendar, fall-festivals
- **Event Name**: River Day 2026
  - **Description**: Mark your calendars for River Day 2026! Join our beloved annual festival celebrating the Westport River and its community, taking place on Saturday, June 20th, from 10 AM to 2 PM at the Head of Westport Town Landing. Hosted by the Westport River Watershed
  - **Interested Audience**:
    - Count: 203
  - **Date**: Sat Jun 20 2026 at 10:00 am (-04:00)
  - **Event URL**: https://allevents.in/westport/river-day-2026/200029850306602
  - **Venue**: 493 Old County Road, Westport, MA, United States, Massachusetts 02790
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czcvYmFubmVycy82ODIxNWVlMWVhMDlmZDhlYWFjNDE0MzlmODZlYTYyNzlkZDJlZDY1YTBhZmRlY2JkNTA1ZWIxMDkzNGE5MWJlLXJpbWctdzEyMDAtaDY3Ni1kY2QxZDllMC1nbWlyP3Y9MTc3NTgwNzg0Mg.avif
  - **Categories**: kids, music, festivals, art, entertainment, sports, live-music, fine-arts, it, calendar, volunteering, music-festivals, parades
- **Event Name**: 8th Annual Maypole Ceremony
  - **Description**: Get ready to dance around the maypole and celebrate spring with fun, friends, and festive vibes!About this EventIt’s time again for our annual Maypole ceremony!  Every year we dance together weaving our intentions around
  - **Date**: Sat May 23 2026 at 06:00 pm – Sat May 23 2026 at 08:00 pm (-04:00)
  - **Event URL**: https://allevents.in/westport/8th-annual-maypole-ceremony/100001985676827845
  - **Venue**: The Heron Center
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czMvYmFubmVycy9lNWQwNDA5YjU2MDk2YzIzZDA0MzE3NGM2OGYxZTQ1ZTg1NzNkMmEzYWI4NGIxZTQxNGE5YmMzYjU4NTE0MmYzLXJpbWctdzEyMDAtaDE2OTctZGM3NjhmNzItZ21pci5qcGc_dj0xNzc0MjM2NzU3.avif
  - **Price**: Free
  - **Categories**: contests, parties, trips-adventures, entertainment, nonprofit

## Trending Events in Westport

- **Event Name**: Showbarn Sessions | Ricky Skaggs & Kentucky Thunder
  - **Description**: Kick off the 2026 Showbarn Sessions season with an unforgettable night of bluegrass at Ashbourne Farms.

Join us Friday, April 17th, for an intimate evening featuring Ricky Skaggs with Kentucky Thunder. 

ABOUT RICKY SKAGGS
A 15-time GRAMMY® Award winner
  - **Venue**: 3810 Old Westport Road, La Grange, KY 40031
  - **Banner**: https://cdn-az.allevents.in/events6/banners/9cea36b31219b1c572fa5835c1f8aaca14932a912a7803b58a942e9276654e2b-rimg-w1200-h672-dc191916-gmir?v=1775860186
- **Event Name**: The 20th Taste of Westport - An American Classic
  - **Description**: CLASP Presents The 20th Taste of Westport - American ClassicWednesday, June 3, 20266:00 PM – 9:30 PMFairfield County Hunt ClubNow celebrating its 20th Annual year, Taste of Westport marks an exciting new chapter as it is hos
  - **Venue**: Fairfield County Hunt Club
  - **Banner**: https://cdn2.allevents.in/thumbs/thumb698a0a7da4198.jpg
- **Event Name**: The Disco Biscuits at Levitt Pavilion
  - **Description**: ✨ Embark on an extraordinary journey at The Disco Biscuits at Levitt Pavilion, where every moment promises to be unforgettable! 🌟 Imagine of transforming Levitt Pavilion in the heart of Westport,
  - **Venue**: Levitt Pavilion
- **Event Name**: Matteo Bocelli
  - **Description**: ✨ Discover the extraordinary at Matteo Bocelli, where magic meets reality in ways you've never imagined! 🏛️ Set in Levitt Pavilion Westport nestled in bustling Westport, CT, this event pr
  - **Venue**: Levitt Pavilion Westport
  - **Banner**: https://cdn-az.allevents.in/events1/banners/8b880ab0-13d0-11f1-89f1-09c30f73298b-rimg-w1000-h1000-dc030202-gmir.jpg?v=1772192184
- **Event Name**: G. LOVE, DONAVON FRANKENREITER, MOON TAXI – ROLLING TOGETHER REVUE TOUR
  - **Description**: TUESDAY, JUNE 23 | 7PM SHOW | 6PM DOORS

Pre-Sale: Tuesday, March 17 at 10am ET

Psst.. Get your 2026 Levitt Pavilion Membership now: Enjoy pre-sale access AND member discounts to this and upcoming shows!*

Public On Sale: Friday, March 20 at 10am ET

PRE
  - **Venue**: 40 Jesup Rd, Westport, CT, United States, Connecticut 06880
  - **Banner**: https://cdn-az.allevents.in/events6/banners/2ee8e28a580c6e6fdcd3964bfc188026cbc354c28b5c0759fb17a5b3de8fefa0-rimg-w1185-h701-dc594220-gmir?v=1775685467
- **Event Name**: 80th Annual Seafood Festival
  - **Description**: 🦀 Westport’s 80th Annual Seafood Festival – A Coastal Tradition Returns! 🌊🎉

Get ready to celebrate 80 years of flavor, fun, and community at one of Westport’s most beloved events! The Seafood Festival is a family-friendly feast featuring fresh local fish
  - **Venue**: Westport Maritime Museum
  - **Banner**: https://cdn-az.allevents.in/events9/banners/e03932d96fcee03d5ae0d07749f837df4dc8a212d026b08eeef32d0f13604a29-rimg-w1200-h800-dc44342f-gmir?v=1775132982
- **Event Name**: 2026 Wine, Cheese & Chocolate Festival
  - **Description**: Join us on June 13, 2026, for an unforgettable day filled with the region's finest flavors at the Wine, Cheese & Chocolate Festival! 

Hosted by the Coastal Wine Group, this exceptional event lets you 
taste over 50 wines from 14 different vineyards,
  - **Venue**: Westport Fair Inc
  - **Banner**: https://cdn-az.allevents.in/events9/banners/32c2b3b3e778fd6848ea88fc6f4a87af0888fa7cabe8ad300765634ea3dfdd3a-rimg-w1200-h663-dcd7dbdd-gmir?v=1774389376
- **Event Name**: Greensky Bluegrass at Levitt Pavilion
  - **Description**: ✨ Experience the magic of Greensky Bluegrass at Levitt Pavilion, where moments become memories that last a lifetime! 🏛️ The iconic Levitt Pavilion in Westport, CT sets the perfect stage
  - **Venue**: Levitt Pavilion
  - **Banner**: https://cdn-az.allevents.in/events9/banners/4907f8b0-219c-11f1-a01a-adaecb19c40b-rimg-w1200-h477-dced4f25-gmir.jpg?v=1773709055
- **Event Name**: Greensky Bluegrass
  - **Description**: 🌟 Step into a world of wonder at Greensky Bluegrass, where extraordinary moments await! 🏛️ Located at Levitt Pavilion Westport in dynamic Westport, CT, this event will become the talk of
  - **Venue**: Levitt Pavilion Westport
  - **Banner**: https://cdn-az.allevents.in/events9/banners/f24938f0-33dd-11f1-97fe-0520c8f1a874-rimg-w800-h1000-dcffffff-gmir.jpg?v=1775716377

## Browse Festivals Events by Date

- [Festivals Events Today in Westport](https://allevents.in/westport/festivals--today)
- [Festivals Events This Weekend in Westport](https://allevents.in/westport/festivals--this-weekend)
- [Festivals Events in April in Westport](https://allevents.in/westport/festivals--april)
- [Festivals Events in May in Westport](https://allevents.in/westport/festivals--may)

## FAQs

- **Q**: What are the top Festivals events in Westport?
  - **A:** 2026 Wine, Cheese & Chocolate Festival (Sat Jun 13 2026 at 11:00 am at Westport Fair Inc), South Coast Harvest Festival 2026 (Fri Sep 25 2026 at 03:00 pm at South Coast Harvest Festival), River Day 2026 (Sat Jun 20 2026 at 10:00 am at 493 Old County Road, Westport, MA, United States, Massachusetts 02790), 8th Annual Maypole Ceremony (Sat May 23 2026 at 06:00 pm at The Heron Center), Hugo The Ultimate Journey Tribute Concert - One night only at CT Food Truck Battles Festival (Sat, 16 May at 07:00 pm at Woodtick Recreation Area).
- **Q**: What are the top free Festivals events in Westport?
  - **A:** 8th Annual Maypole Ceremony (Sat May 23 2026 at 06:00 pm at The Heron Center).
- **Q**: How can I find Festivals events in Westport?
  - **A:** You can discover upcoming Festivals events in Westport on AllEvents.in. Browse by date, venue, or price to find events that match your interests.
- **Q**: How do I buy tickets for Festivals events in Westport?
  - **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 Festivals events in Westport?
  - **A:** Some popular venues hosting Festivals events in Westport include Westport Fair Inc, South Coast Harvest Festival, 493 Old County Road, Westport, MA, United States, Massachusetts 02790.
- **Q**: What is the price range for Festivals events in Westport?
  - **A:** Prices for Festivals events in Westport range from USD 39 to USD 39. Many events also offer free entry.
- **Q**: Who are the top organizers for Festivals events in Westport?
  - **A:** Popular organizers hosting Festivals events in Westport include Coastal Wine Trail, South Coast Harvest Festival, Westport River Watershed Alliance.
- **Q**: Are there any online Festivals events available?
  - **A:** Yes, many Festivals 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 Festivals events in Westport?
  - **A:** Follow the Festivals category on AllEvents.in to get notified when new Festivals events are listed in Westport.

## Category Banner

- **Banner Image**: https://cdn2.allevents.in/transup/6e/5415e403f74b77938c0695ac11464e/Festival.jpg

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