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Ana & Will's Wedding Weekend

September 5th and 6th, 2025
The Berkshires, Massachusetts

THE NIGHT BEFORE

WELCOME DRINKS

THE WYNDHURST MANOR
Lenox, MA

Friday, September 5th, 2025
8PM - 10PM
Following Rehearsal Dinner

MORE INFO

WEDDING DAY

CEREMONY

CHESTERWOOD ESTATE
Stockbridge, MA

Saturday, September 6th, 2025
5PM
Reception to Follow

MORE INFO

WEDDING DAY

AFTERPARTY

LIFEHOUSE BERKSHIRES
Lenox, MA

Saturday, September 6th, 2025
11PM - 1AM
Following Reception

MORE INFO

THE NIGHT BEFORE

Please join us for an evening of welcome drinks as our celebration begins at the Wyndhurst Manor.

WELCOME DRINKS


Friday, September 5th, 2025
55 Lee Road, Lenox, MA 01240

8:00 PM to 10:00 PM

Cocktail Attire

PARKING


The welcome drinks venue is located 5-10 minutes from the recommended accommodations and offers abundant parking.

The Wedding Day

AN EVENING OF CELEBRATION

Together with their families, Ana and Will request the honor of your presence at their marriage.

CEREMONY

The Chesterwood Estate

4 Williamsville Rd, Stockbridge, MA 01262

Please plan to arrive by 4:45, as our ceremony will begin at five o'clock. Join us from 4:30 for champagne and gathering.

Creative Black Tie

A NOTE ON TRANSPORTATION

For an effortless arrival and departure, we've arranged private shuttle service between our venue and the recommended Lenox and Pittsfield area accommodations.

DESIGNATED TRANSPORTATION
Given the Berkshires' limited Uber availability, we encourage you to take advantage of our shuttle service—allowing everyone to relax and enjoy the celebration fully.

Departure
Our shuttle service will depart promptly between 3:45pm and 4:15pm from the five recommended hotels. More information on shuttle departure times coming soon! :)

Return
At the evening's close, private transportation will depart for the five hotels. Each vehicle will be marked with its destination. Please see "Accommodation Information" below for more information on hotel transportation.

IF YOU'RE DRIVING
The estate offers parking, connected to our venue by a garden path. Please allow 10 minutes for this brief walk to the entrance.


Please keep these details in mind as you plan your stay in the Berkshires.

FREQUENTLY ASKED QUESTIONSACCOMMODATION INFORMATION

THE DRESS CODE

The Night Before

Cocktail Attire

THE WEDDING

Creative Black Tie

THINK: BLACK TIE ATTIRE WITH A CREATIVE & DRAMATIC TWIST ✨

Set at sculptor Daniel Chester French's stunning summer estate, this celebration calls for statement-making formal wear - whether that's vintage glamour, modern runway, old-world opulence, or any other bold fashion era or style. Express yourself in any color (except white ;)), mix traditional with modern, and don't be shy with accessories.

For separates, consider tuxedos or creative formal alternatives - don't feel like you need to stick to the traditional black tux! Colors, patterns, and texture varieties encouraged! For gowns and formal jumpsuits, similarly consider rich textures, striking silhouettes, and extravagant details.

The more dramatic, the better.

SIDE NOTE: If this has you clutching your pearls in horror and/or breathing into a paper bag, rest assured traditional black tie is wonderful (no one will side-eye you for not wearing a hat made of live butterflies). This is just my invitation for extra-ness because I love seeing everyone's unique style & love any excuse to go all out (because I consider that to be fun, lol). If classic black tie is more your vibe, that works too. So excited to celebrate – the rest is just fabric and fun!! ✨ - ana <3

✨ Link for Dress Code Inspiration ✨🤩

Pinterest

TRAVEL

AIRPORTS



The closest airport to the Berkshires is Albany International Airport in Albany, New York - a little less than 1 hour to the venue/hotels in the Lenox area. If you're flying, the fastest option would be into Albany and rent a car.

Other airport options, organized by approximate driving distance to Lenox:

Hartford Bradley Airport (CT): 1hr30 drive

Tweed New Haven Airport (CT): 2hr drive

Rhode Island T.F. Green Airport (Providence): 2hr15 drive

LaGuardia Airport (NYC): 2hr45 - 3hr drive

Boston Logan Airport: between a 2.5-3.5hr drive (depending on time/day)

Manchester Airport (NH): Similar to Boston, might save time avoiding city commuter traffic

JFK Airport (NYC): about a 3hr drive

Newark Airport (outside NYC): similar to JFK, might save time avoiding city commuter traffic

DRIVING

From Boston: 2hr30-3hr45
This can vary widely because of Boston commuter traffic and the smaller highways from Boston out to the Berkshires. The best time to drive would be early morning, 11am-1:30pm, or after 7pm.

From NYC: About 3hrs? We'll leave the more concrete estimations to experienced NYC travelers.:)

From Chicago (plz don't do this <3): 13 hours

ACCOMMODATION

Transportation will be provided to and from the following five hotels on the wedding day (09/06):

(We have room blocks at four of the five hotels below. Please follow "booking link" for group pricing and availability)

LifeHouse Berkshires

194 Pittsfield Rd, Lenox, MA 01240

*Note: this is where the afterparty will be held from 11pm-1am on 09/06.

Booking LinkWebsite

The Hilton Garden Inn

1032 South St, Pittsfield, MA 01201

Booking LinkWebsite

The Hotel On North

297 North Street, Pittsfield, MA 01201

Booking LinkWebsite

The Holiday Inn & Suites

One West St, Pittsfield, MA 01201

Booking LinkWebsite

Hampton Inn & Suites

445 Pittsfield Rd, Lenox, MA 01240

Please note: While we do not have an official block at the Hampton Inn, we will offer shuttle pickup/dropoff here and encourage guests to book through the normal website (linked below)!

Website

A Note on Transportation:

For those staying at accommodations other than these five hotels, you have a couple of options!

You're welcome to park at any of our shuttle pickup hotels, or walk to the nearest pickup hotel if you're close by. The same goes for the return trip - feel free to take the shuttle to one of these hotels or to the afterparty at Lifehouse. There will also be transportation home from the afterparty to the other four hotels.

While ride-sharing services are an option in the Berkshires, availability can be limited, especially during peak times - so please plan accordingly if this is your preferred method. Our shuttle service will operate exclusively between the venue and these five hotels.

Don't forget to note if you'll be using the shuttle service in your RSVP!

YOU MEAN THE WORLD TO US!

Your presence at our special day is the greatest gift of all! If you'd like to help us begin our married life together, we have a wedding wish list!

WE'VE GOT ANSWERS

WILL THE CEREMONY BE OUTSIDE?

Yes! A light jacket is advised in case of inclement weather. The reception is tented and has a full floor (so no worries about heels getting stuck in the grass as the night goes on! :))

CAN I BRING MY CHILDREN?

Our celebration is designed as an adults-only event, and our guest list is limited to those specifically named on the invitation. This decision was made with careful consideration of our historic venues and their capacity restrictions. We appreciate you making arrangements for childcare and look forward to celebrating with you.

CAN I TAKE PHOTOS DURING THE CEREMONY?

We kindly ask that there are no phones or cameras during our wedding ceremony. We receive sneak pictures from our dedicated photographers within 48 hours, and we will upload ASAP to this website!

WILL THERE BE PARKING AVAILABLE?

There will be plenty of parking available on site along with complementary transportation to and from the venue from room block hotels in the Lenox and Pittsfield areas. Please plan to arrive early if you need to park.

WILL THERE BE VEGETARIAN OPTIONS?

Yes! We will have a variety of options to meet everyones dietary needs.

CAN I BRING A PLUS ONE?

We've reserved a spot for those specifically named on your invitation. If your invitation includes "and Guest" or your partner's name, we would love to have them join! If not, we kindly ask that you respect our guest count.

WHEN IS THE RSVP DEADLINE?

Please RSVP by August 1st.

IF WE STAY AT AN AIRBNB OR ACCOMODATION NOT LISTED ON THE WEBSITE, ARE THERE UBERS TO BRING US TO THE WEDDING AND/OR HOME?

PLEASE NOTE THERE ARE LIMITED UBERS IN THE BERKSHIRES, ESPECIALLY AT NIGHT. If you stay somewhere outside Lenox or the listed hotels (where transportation is provided), please keep this in mind. We recommend staying in Lenox, as many hotels are walkable. If you plan to Uber to the wedding, please leave a gracious amount of time to find one.

RSVP BELOW

KINDLY REPLY BY AUGUST 01

THE WEDDING

THE NIGHT BEFORE

Add Invited Guest

Wedding Afterparty RSVP: The celebration continues until 1am at a separate location. Please only RSVP 'yes' if you're sure you can make it.

Where will you be staying?