Bennington Events

Click on any month to see what’s happening in Southern Vermont!

January

... A Winter  Wonderland of things to do.

Oldcastle Theatre Company Winter Concert Series

2018 Dates to be determined

Vermont Arts Exchange Basement Music Series

2018 Date to be determined
Masonic Hall, North Bennington, Vermont
Doors open @ 7 Show starts @ 8

Winterfest and Penguin Plunge

2087 Date to be determined
Plunge Time: 11:00 am Lake Paran North Bennington, Vermont Join Special Olympics Vermont for the Annual North Bennington Penguin Plunge.  Brave the icy waters of Lake Paran to raise awareness and funds for the 935 athletes of Special Olympics Vermont.  For more info:  www.specialolympicsvermont.org

February

... Opportunities abound for your favorite winter outdoor activity: skating,  skiing, showshoeing, snowmobiling.

Bennington Museum Student Art Show

February 2 – March 19, 2017
75 Main St, Bennington, Vermont
View artwork from talented students from preschool to grade 12.

East Coast Snocross

February 18-19, 2017 at 10:00am
Willow Park, Performance Drive, Bennington, Vermont
Returning for the second year in a row to the Green Mountain area of Bennington.

Oldcastle Theatre Movies

Thursdays at 7pm, tickets are $5.00
331 Main St, Bennington, Vermont
Enjoy these comedy classics:
February 16 – Tootsie
February 23 – M*A*S*H

School Vacation Theatre Camp

February 20-25, 2017 from 12:30pm to 2:30pm
Oldcastle Theatre, 331 Main Street, Bennington, Vermont
Oldcastle’s School Vacation Theatre Camp is a unique experience for kids to enjoy during their school break. Click on the link above for more information or to register your kids.

Matt Edwards and Buck2Fifty

February 24, 2017
Oldcastle Theatre, 331 Main Street, Bennington, Vermont
Doors open at 7:00pm, Show starts at 8:00pm
Tickets are $25 for Adults, $12 for Students

Vermont Arts Exchange Basement Music Series

The Prescription with Side Effects Horn Section
February 25, 2017
Masonic Hall, 504 Main Street, Bennington Vermont
Doors open at 7:00pm, Show starts at 8:00pm
Tickets are $18 in advance, $22 at-the-door and $10 for Students

Music at the Museum – Beethoven to Bennington (and back again!)

February 26, 2017 at 2:00pm
Bennington Museum Ada and Paul Paresky Wing, 75 Main Street, Bennington, Vermont
Bennington Museum begins the 2017 Music at the Museum concert series with From Beethoven to Bennington (and back again!), a performance by cellist Maxine Neuman and friends.

March

March is sugaring time in Vermont.  See it being made, or just enjoy it on your pancakes...

St.  Patrick’s Day Parade

March 12, 2017
1:00pm Parade begins on Depot Street
Downtown Bennington, Vermont

Southern Vermont Wings & Winter Homebrew Festival

March 18, 2017
Festival goes from 12:00pm-4:00pm
Masonic Lodge, 504 Main Street, Bennington, Vermont
Tickets are $30. Come enjoy the areas best wings and home brewed beer! Click the link above for more information or to buy your tickets.

Vermont Arts Exchange Basement Music Series

Billy Wylder
March 25, 2017
Masonic Hall, 504 Main Street, Bennington Vermont
Doors open at 7:00pm, Show starts at 8:00pm
Tickets are $18 in advance, $22 at-the-door and $10 for Students

Maple Sugaring Open House Weekend

March 25-26, 2017
Bennington, Vermont
Open House Weekend is your opportunity to get a first-hand look at how Vermont’s sugar makers are able to take the sap from maple trees and craft something as delicious as pure Vermont maple syrup! Click here for maps and directions:  vermontmaple.org

April

April flowers are so welcome after a long winter.

School Vacation Theatre Camp

April 17-21, 2017 from 12:30pm to 2:30pm
Oldcastle Theatre, 331 Main Street, Bennington, Vermont
Oldcastle’s School Vacation Theatre Camp is a unique experience for kids to enjoy during their school break. Click on the link above for more information or to register your kids.

May

Tour of the Battenkill Bicycle Race

May 20, 2017
Start in Greenwhich, New York to Bennington, Vermont
One of the largest cycling events in the United States will come to our area for its 13th anniversary in 2017.  More than 3,000 participants from 45 states and 15 countries compete in the Tour.  Race distance for most of the amateur categories is 65 miles, while for the Pro and Category 1 and 2 racers it’s 84 miles.  There will be races for cyclists in amateur and professional rankings on Sunday, as well as a pro/am event.

Mayfest Arts & Crafts Festival

May 27, 2017
10:00 AM
Main St. Bennington, Vermont
Downtown Bennington transforms into a festival of arts, crafts, activities, food, & entertainment.  In 2014 there will be over 125 crafters and artisans from throughout New England featuring handmade crafts of wood, pottery, glass, metal, fabric, jewelry, and more.  As always, School Street will be lined with ethnic treats including Indian, German, Italian, and American.  You’ll also find favorites such as fried dough, gourmet seafood, wood fired pizza, baked potatoes, ice cream, and more!  Mayfest isn’t just for adults though; there are lots of kid’s activities, contests, and games.  The Vermont National Guard climbing wall is always one of the biggest kid’s attraction along with football toss and dunking booth.  The 4-H shooting range, face painting, and more also add to the fun.  Click for more info: www.betterbennington.com

Hemmings Cruise-Ins Car Shows 2017

5:30 – 8:00 PM (Dates Below)
Main St, Bennington, Vermont

  • Thursday,  May 11
  • Thursday,  May 25
  • Thursday,  June 8
  • Thursday,  June 22
  • Friday,       July 14
  • Thursday, July 20
  • Thursday,  August 3
  • Thursday,  August 17

June

Strolling of the Heifers Weekend

June 2-4, 2017
Main St. Brattleboro, Vermont
Join us in beautiful, historic Brattleboro for a weekend of activities honoring farmers and celebrating local food, all built around our signature event, the world-famous Strolling of the Heifers Parade, Saturday, June 3 at 10 a.m. sharp! All Strolling of the Heifers events are rain or shine! The heifers don’t mind the weather, the farmers are working in all kinds of weather, and we will be honoring and celebrating them all weekend!  For a complete schedule of events, click here: www.strollingoftheheifers.com   About 40 minutes east of Four Chimneys Inn.

Hemmings Cruise-Ins Car Shows 2017

5:30 – 8:00 PM (Dates Below)
216 Main St. Bennington, Vermont

  • Thursday,  May 11
  • Thursday,  May 25
  • Thursday,  June 8
  • Thursday,  June 22
  • Friday,       July 14
  • Thursday, July 20
  • Thursday,  August 3
  • Thursday,  August 17

Graduation, Williams College

June 4, 2017
Williamstown, MA
Click here for more info:  www.commencement.williams.edu

 

July

Bennington’s “First Fridays” Event

July 7, 2017
5:00 PM – 8:00 PM
Downtown Bennington Historic District, Bennington, Vermont (map)
Located 1.3 miles from Four Chimneys. Come celebrate the Arts on the First Friday of each month with a Gallery Tours and Artist Openings, Live Entertainers and Street Performers, Children’s Activities, Oldcastle Theater Productions, and More! First Friday Programs and Maps available at the Better Bennington Corporation and most downtown shops on the day of the event.

Hometown 4th of July Celebration and Fireworks

July 4, 2017
Willow Park, Bennington, Vermont (map)
2.7 miles from Four Chimneys

Hemmings Cruise-Ins and Car Shows 2017

5:30 – 8:00 PM (Dates Below)
216 Main St. Bennington, Vermont (map)

  • Thursday,  May 11
  • Thursday,  May 25
  • Thursday,  June 8
  • Thursday,  June 22
  • Friday,      July 14
  • Thursday, July 20
  • Thursday,  August 3
  • Thursday,  August 17

Midnight Madness

July 20, 2017
7:00 PM-12:00 AM
Main St. Bennington, Vermont
Downtown retail extravaganza that is a terrific family even and community institution with incredible bargains all throughout downtown.

 

 

August

Bennington Arts Weekend

August 4-6, 2017
Downtown Bennington, Vermont
A weekend of museum and gallery exhibits, along with music and theater taking place throughout downtown Bennington. For more information contact The Better Bennington Corporation at admin@betterbennington.com or at (802) 442-5758.

Southern Vermont Arts and Crafts Festival

August 4-6, 2017
10:00 AM-5:00 PM
Camelot Village, 66 Colgate Village, Bennington, Vermont
Bennington’s 38th annual craft festival is a exhibition of fine artisan goods from around the area. Adult admission is $8 a day or $12 for the weekend, Kids admission is $2.

Bennington’s “First Fridays” Event

August 4, 2017
5:00 PM–8:00 PM
Downtown Bennington Historic District, Bennington, Vermont  (map)
Celebrate the Arts on the First Friday of each month with a Gallery Tours and Artist Openings, Live Entertainers and Street Performers, Children’s Activities, Oldcastle Theater Productions, and More! First Friday Programs and Maps available at the Better Bennington Corporation and most downtown shops on the day of the event.

Bennington Battle Day Festivities 2017

August 12-13, 2017
Bennington Battle Monument, Bennington, Vermont (map)
Located .7 mile from Four Chimneys Inn, Bennington Battle Day is a time to remember the Battle of Bennington, a battle that lead to the turning point in the Revolutionary War in the 18th century.  Visitors and locals alike can ride an elevator to the top of the Bennington Monument for panoramic views of the valleys and the hills of Vermont, Massachusetts and New York. The stone monument, which is about 306 feet (about 93.3 meters) above the streets of Bennington, marks the site of a critical supply depot for the Green Mountain Boys during the Revolutionary War.

Rock, Rattle, and Drum Pow Wow

August 12-13, 2017
10:00 AM-6:00 PM
325 North St. Bennington, Vermont
Award Winning, Arvel Bird &The Aztec Dancers!

 

Hemmings Cruise-Ins and Car Shows 2017

5:30 – 8:00 PM (Dates Below)
216 Main Street, Bennington, Vermont (map)

• Thursday, May 11
• Thursday, May 25
• Thursday, June 8
• Thursday, June 22
• Friday, July 14
• Thursday, July 20
• Thursday, August 3
• Thursday, August 17

September

Bennington’s “First Fridays” Event

September 1, 2017
5:00 PM–8:00 PM
Downtown Bennington Historic District, Bennington, Vermont (map)
Located 1.3 miles from Four Chimneys Inn.  Celebrate the Arts on the First Friday of each month with a Gallery Tours and Artist Openings, Live Entertainers and Street Performers, Children’s Activities, Oldcastle Theater Productions, and More! First Friday Programs and Maps available at the Better Bennington Corporation and most downtown shops on the day of the event. For more information visit www.betterbennington.com

Garlic & Herb Festival

September 2-3, 2017
10:00 AM–5:00 PM
Camelot Village, Rte 9 West, Historic Bennington, Vermont (map)
Garlic Growers, Food Producers, Crafts, Garlic Products, Garlic Ice Cream, Garlic Apple Pie, Beer Tent, Live Music, Informative Demonstrations including Garlic Braiding, Children’s Activities, Weed Walk and much more! A Top Ten Vermont Event which draws thousands of visitors. Join the fun at lovely (located just across the street from Four Chimneys Inn) Free Parking. Admission is $5 for adults. Private Property – please leave pets at home. Close to Bennington’s historic and cultural attractions. For more information call the Bennington Area Chamber of Commerce at (802) 447-3311 for suggested itineraries and accommodations.

American Lung Association Fight for Air Climb

September 9, 2017
Bennington Battle Monument, Bennington VT
Help raise funds to benefit  lung disease while reaching a personal goal!

Annual Bennington Quiltfest

September 16-17, 2017
Saturday: 9:00 AM-5:00 PM, Sunday: 9:00 AM-4:00 PM
Mount Anthony Union Middle School, 747 East Road, Bennington, Vermont (map)
Located 1.8 miles from Four Chimneys Inn. For more info:  www.benningtonquiltfest.com

October

Bennington’s “First Fridays” Event

October 6, 2017
5:00 PM– 8:00 PM
Downtown Bennington Historic District, Bennington, Vermont (map)
Located 1.3 miles from Four Chimneys Inn.  Celebrate the Arts on the First Friday of each month with a Gallery Tours and Artist Openings, Live Entertainers and Street Performers, Children’s Activities, Oldcastle Theater Productions, and More! First Friday Programs and Maps available at the Better Bennington Corporation and most downtown shops on the day of the event.

Oktoberfest

October 7, 2017
11:00 AM-5:00 PM
Colgate Park, Rout 9 West, Bennington, Vermont

Enjoy live music, food, beer, vendors and children’s activities. Admission is $5, children under 12 are free

Bennington’s Fallapalooza!

October 28, 2017
11:00 AM–4:00 PM
Main Street, Bennington, Vermont (map)
Located 1.3 miles from Four Chimneys Inn, it’s like Mayfest, Midnight Madness, Octoberfest, and the Food Festivals all wrapped up into one big celebration! Enjoy Bennington Farmers Market, Wagon Rides, Crafters and Vendors, Entertainers, Children’s Activities, Store-to-Store Trick-or-Treating, Food Vendors, and more. Main Street in Downtown Bennington. Free admission and free parking.

November

Veteran’s Day Parade

November 11, 2017
11:00 AM
Main St. Bennington, Vermont

Hometown Holiday

November 25, 2017
10:00 AM–5:00 PM
Downtown Bennington Historic District, Bennington, Vermont (map)
Located 1.3 miles from Four Chimneys Inn.Visit with Santa Claus and celebrate “Small Business Saturday” while enjoying the Sounds of the Season with Carolers and Musicians. Many in-store specials and activities all throughout downtown Bennington. Check out www.betterbennington.com for details.

 

December

New Year’s Eve Bash

For those looking for live music take a look at Mount Anthony Country Club just a two minutes drive from the inn.

2017 New Years Eve Party at Mount Anthony Country Club
Live Band: Crescente
Saturday, December 31, 2016
9pm – 1 am
$15 in advance / $20 at door
p) 802-442-2617
Call directly for tickets and more information.
Book dinner at The Grille at Mount Anthony Country Club before the party!
180 Country Club Road
Bennington, Vermont


January, February, April, May, July, August, September banner photos courtesy of  “The Shires of Vermont C Lee Krohn, 2008”