Schedule
Friday, October 3, 2025
Berkshire Hike
9:15 am - 12:00 pm
Adams, MA 01220
See the beautiful Berkshires in the fall!
Tom and Ilana's third in-person date was a hike in the Berkshires. It's your turn to enjoy panoramic views of the Berkshires atop the highest point in Massachusetts (weather dependent). We'll be leading two hikes. Ilana's is easy-to-moderate and allows hikers to start at the top of Greylock and explore trails around the summit. Tom's hike is moderate, starts below the summit, and follows Ilana's loop around the summit. We'll hit the trails at 9:30, so we recommend arriving by 9:15! We recommend you bring hiking shoes/sturdy sneakers, water, sunscreen, bug spray with deet, and hiking snacks. Ilana's Hike: https://www.alltrails.com/trail/us/massachusetts/mount-greylock-overlook-trail Google Maps Parking Coordinates: 42.63715, -73.16718 Tom's Hike: https://www.alltrails.com/trail/us/massachusetts/mount-greylock-via-sperry-road-and-hopper-trail Google Maps Parking Coordinates: 42.62444, -73.19044
Welcome Winery/Brewery Crawl
5:00 pm - 8:00 pm
146 Flints Crossing Road, Canaan, NY 12029
Casual, but wear your drinking pants....
Home Range Winery -> Balderdash Cellars -> Antimony Brewing Home Range does not have food, but Balderdash usually has a food truck and Antimony has a kitchen. After starting at Home Range at 5pm, we'll aim to arrive at Balderdash around 6pm and Antimony around 7pm, though this is a pub crawl so these latter two times are approximate! For that reason we recommend you start with us at Home Range. Home Range Winery: https://homerangewinery.com Balderdash Cellars: https://balderdashcellars.com Antimony Brewing: https://www.antimonybrewing.com/menus
Saturday, October 4, 2025
Bloody Marys
12:00 pm - 1:45 pm
12 Pleasant St, Adams, MA 01220
Tom and Ilana's favorite Bloody Mary that essentially comes with its own appetizer platter on top. Tom and Ilana decided to get married over a couple of these Bloody Marys! Feel free to order that or anything else on this sneaky good menu. For menu and pricing, please see here: https://ajstrailsidepub.com/menu Hot tip: Pair this with the Ashuwilliticook Rail Trail for a nice bike/walk before or after.
MASS MoCA
2:00 pm - 4:00 pm
One of Tom's favorite museums, this gem is a crown jewel of the Berkshires.
This is a suggested meeting time for those who are interested in exploring this amazing modern art museums in North Adams! There is no official tour, so please just show up and enjoy the museum around this time! FYI Tom may need to miss out on this in preparation for the Jamboree, so please don't wait up for him!
Floral Arranging with Ilana
2:30 pm - 4:30 pm
2541 Hancock Rd, Williamstown, MA 01267
You Belong Among the Wildflowers....
A favorite hobby of Ilana's with some of her favorite people! Enjoy some sensible day drinking and flower arranging with Ilana. Your arrangements will become centerpieces for the wedding!
Welcome Jamboree
7:00 pm - 9:45 pm
866 Cold Spring Road, Williamstown, MA 01267
Calling all of our talented, musical friends!
Music is one of the biggest areas of passion where Tom and Ilana overlap. They have so many musical friends (yes, you!) and are hoping for a night where we bring them all together, with a few speeches thrown in there. Tom will play a set with the Corey Hill Sax Quartet. Following that will be the Request Room! The Request Room is a very unique karaoke experience that Tom was a part of while living in Northampton. Ilana will sing, and you can too! Any and all requests attempted! We will provide a dessert bar. Given our guest count and the modest kitchen at the '6 House Pub, we ask that you please have dinner prior to the Jamboree. Feel free to dine ahead of time at the '6 House Pub, or please see our FAQ page for additional options! Attire is dressy casual - think a Tanglewood concert or a nice picnic.
Sunday, October 5, 2025
Wedding
4:00 pm - 10:00 pm
2422 Hancock Rd, Williamstown, MA 01267
Formal and Festive Attire Welcome!
Think suits, dresses, gowns, and formal attire - wear anything but white, dancing shoes are mandatory! Open bar but please tip your bartenders well!