Legendary Tales. Timeless Engagement.

The Wayside Inn is a one-of-a-kind destination for special programs and events that will connect you with history in ways that will delight you. Explore our calendar below.

**SOLD OUT** Jerusha’s Halloween Ball 2023

Tickets for Jerusha’s Ball 2023 are now sold out. If you are interested in attending and would like to add your name to our waiting list, please send an email to TWIF@wayside.org with the subject line “Waiting List for Jerusha’s Ball”. Please include your name, number of tickets needed, and the best way to reach you (email or phone). Should we have cancellations those on the waiting list will be called in the order that emails were received. Thank you.

Friday, October 27th ~ 7pm – 10pm
$100 without costume, $85 with costume, members $10 off
$20 tarot card readings

Have some spirited fun with The Wayside Inn Foundation at our 2023 Jerusha’s Halloween Ball fundraiser, a costume party with generous appetizers and beverages, dancing, music by DJ Backspin, and a wine & whiskey pull. Popular last year tarot card readings with Beyond the Gate and whiskey tastings will make a return. Last year’s attendees set the costume creativity bar high so we will once again hold a costume contest with prizes for Most Creative, Most Historic, and Most Legendary. Bring your best! If costumes aren’t your thing, not to worry – we just want to see YOU there.

Want to stay overnight? Book your rooms at The Wayside Inn now for Jerusha’s Ball! We have a block of rooms available at Longfellow’s Wayside Inn for Friday, October 27th (1 king, 1 queen, & 2 full rooms). Price: $180 + tax ($201.06 total). Includes breakfast in the tap room the next morning! Please call LWI’s reservation desk to make arrangements (978) 443-1776.

If rooms at The Wayside Inn sell out, we have a block of rooms held at The Fairfield Inn Boston Sudbury, right around the corner from The Wayside Inn at 738 Boston Post Road. Book your rooms there by October 5th using this link. Questions about staying at The Fairfield Inn? Call their reservations desk directly at 978/443-2223 and be sure to mention Jerusha’s Halloween Ball to get the discounted rate.

Cancellation Policy: No refunds will be issued for cancellations made after Friday, October 20th.


The event is finished.


Oct 27 2023


7:00 pm - 10:00 pm

More Info



Longfellow's Wayside Inn Event Tent
Longfellow's Wayside Inn
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