Apple Fest 2025

The Wayside Inn Foundation (TWIF) is hosting our signature community event, Apple Fest Family Day, this year on September 20, 2025. More than just a festival, Apple Fest Family Day draws over 2,000 attendees from across the MetroWest area for a free, family-friendly day of educational activities, live entertainment, food, and fun across our 100-acre campus. We partner with local nonprofits, educators, artisans, and farms to provide:<ul><li>Live performances, historical demonstrations, and family storytelling</li><li>Petting zoos, hayrides, and obstacle courses</li><li>Educational activity booths tied to New England history, agriculture, and cultural heritage</li><li>Participation from dozens of craft and food vendors</li><li>Community nonprofit showcases, providing visibility and shared impact</li></ul>Interested in supporting at Apple Fest Family Day as a Sponsor? Email to Catherine Whitney at cwhitney@wayside.org or call 978-295-1716. (Rain date: Sunday, September 21, 2025)

The Wayside Inn

Wayside 5k For Scholarships

The Marlborough Regional Community Foundation, a 501(c)(3) non-profit organization, invites you to join the&nbsp;Marlborough Regional Community Foundation Road Race&nbsp;- returning this year in partnership with&nbsp;The Wayside Inn Foundation.&nbsp; This exciting event will bring together runners, walkers, and community supporters - and most importantly, it will directly benefit high school seniors across our region through scholarships that help pave the way for their future success. Saturday, September 20, 2025 8am Start Join us for a fall race day at the Martha Mary Chapel, Sudbury, MA Best of all, the Race is on the morning of Apple Fest Family Day at The Wayside Inn! Stay after the 5K to enjoy food, fun, games, music, and educational activities for the whole family! The celebration starts at 10 AM and ends at 2 PM.

Martha Mary Chapel

Caymus Wine Dinner

Enjoy an exquisite meal paired with Caymus Napa Cabernet, Mer Soleil Silver Unoaked Chardonnay and other wines chosen by our chef.

Jaguar Club Road Show at The Wayside Inn

Stop by The Wayside Inn 9am-5pm to see a roadshow of vintage Jaguar cars brought to you by The Jaguar Association of New England! There will be refreshments and music.

Longfellow's Wayside Inn

Roaring '20s Ball & Casino Night

All Tickets: Members ($90) General ($100) VIP ($250) Tickets are all inclusive of tax &amp; gratuity. All sales are final. No refunds. Event is 21+. ID required for alcohol purchase. Come join us in celebrating our 2nd Annual Roaring '20s Ball with live music from The Cat Nip Junkies! Come dressed in 1920's apparel! Passed apps &amp; dessert with be served. Cash bar available. Photo booth, Casino &amp; live online auction at event! Tickets: VIP Ticket ($250) (LIMITED!) Includes: Speak Easy Themed Pre-party at The Wayside Inn's Front Parlor from 6-7pmEST (doors to main event open at 6:45pm) Special cocktail will be served along passed apps Casino chips to be used at the event General Admission Ticket ($100) Includes: Access to early entry for event at 6:45pmEST Boston Harbor Distillery Sampling (1) ticket Champagne Welcome Toast 1920's themed passed apps Live music by New Orleans themed band, The Cat Nip Junkies! Access to Photo Booth during event Access to Casino with donation Member Ticket ($90) (Includes General Admission access. Members please call 978-443-1776x1. )

The Wayside Inn Foundation

Printing Press Demo with Andy Volpe

About $25| General Tickets (Visit Resy.com) $20| TWIF Member Tickets (call 978-443-1776x1) Andy Volpe is a living historian, copperplate engraving printmaker, and artist in the Worcester MA area.&nbsp;&nbsp;He has been involved with the Museum of Printing in Haverhill MA since 2009, where he researches, presents, and demonstrates printing technology, graphics and illustration printing from 1440s to 1800, Since 2012 he has been working with Gary Gregory who founded the Printing Office of Edes &amp; Gill formerly in Boston, now at the Museum of Printing, which replicates documents and prints of the American Revolution using fully accurate replicas of 18th century presses and type.&nbsp;&nbsp;Volpe researches and replicates the copperplate engraving prints of none other than Paul Revere and other notable 18th century intaglio prints.&nbsp;&nbsp;He also presents on ancient arms, armor, and archaeology at the Worcester Art Museum (Higgins Armory collection) and to area schools, libraries, and at historical “timeline” events throughout New England.

Historic 1700s Colonial Dinner

$65 | Per Person ($10 off for those who dress up in colonial attire!) $55 | TWIF members (Please call the Inn at 978-443-1776x1) This event is non-refundable. Each ticket includes taxes and gratuity. Alcohol served to 21+ only. About: Come celebrate with us at The Historic 1700's Colonial Dinner presented by The Wayside Inn. 5:30pm-Guest Arrival &amp; Cocktail Hour Coow Woow upon arrival, possible Sudbury Ancient Fifes playing during cocktail hour. Cash bar available. 6:15pm-Historic discussion around what led to the Revolutionary War &amp; Sudbury's involvement. 6:30pm-Presentation and served first course. Colonial Clam Chowder, Basket of Corn Muffins &amp; Anadama bread. Buffet Dinner to follow: (includes authentic food from early 1700's) Fricasse of Chicken with pastry crust Ye Olde Beef Stew Traditional Colonist's Haddock with cream sauce Mashed potatoes Root vegetables 8:00pm-Dessert includes Ye Olde apple pie with whipped cream

$65 | Per Person ($10 off for those who dress up in colonial attire!) $55 | TWIF members (Please call 978-443-1776x1) This event is non-refundable. Each ticket includes taxes and gratuity. Alcohol served to 21+ only. About: Come celebrate with us at The Historic 1700s Colonial Dinner presented by The Wayside Inn. 5:30pm-Guest Arrival &amp; Cocktail Hour Coow Woow upon arrival, possible Sudbury Ancient Fifes playing during cocktail hour. Cash bar available. 6:15pm-Historic discussion around what led to the Revolutionary War &amp; Sudbury's involvement. 6:30pm-Presentation and served first course. Colonial Clam Chowder, Basket of Corn Muffins &amp; Anadama bread. Buffet Dinner to follow: (includes authentic food from early 1700's) Fricasse of Chicken with pastry crust Ye Olde Beef Stew Traditional Colonist's Haddock with cream sauce Mashed potatoes Root vegetables 8:00pm-Ye Olde apple pie with whipped cream

Fireside Chat with Paul Revere

Paul Revere Fireside Chat Thursday, March 20, 2025 6-8pmEST 5:30pm-Guest Arrival &amp; Apps 6pm-7:30pm-Fireside Chat Presentation with Paul Revere! 7:30-8pm-Q&amp;A Meet the Interpreter $25 | General Public $20 | Ticket for TWIF Members &amp; Paul Revere House Members All members, please call the Inn at 978-443-1776x1. Join Paul Revere (as portrayed by Interpreter Michael Lepage) by the fireside at the Wayside Inn for a spirited review of the notoriously inaccurate Longfellow poem that immortalized his Midnight Ride. Heavy apps included with the price of a ticket. Drinks available for purchase at the Tavern Bar.

Pre-St. Paddy's Day Luncheon

12:00pm: Reception Assortment of cheese with a pint of Guinness! 1:00pm: Dinner Shamrock Caesar Salad with Croutons Guinness Braised Short Ribs with Cheddar Whipped Potatoes &amp; Roasted Carrots &amp; Parsnips Trifle Cake Cup with Sponge Cake, Fresh Fruit, Custard &amp; Whipped Cream Homemade Irish Cream 1:30pm: Performance We will be joined by dancers from the Inishfree School of Irish Dance, in Concord, MA to perform some traditional Irish step dancing! Guests might even get the chance to join the dancers on the dance floor and learn a real Irish Ceili dance!

The Wayside Inn 

Jerusha's Halloween Ball

Join The Wayside Inn Foundation for some spirited fun at Jerusha’s Halloween Ball fundraiser! Last year’s JBall sold out, so don’t miss your chance to join this year’s costume party. Enjoy generous appetizers and beverages, dance to music by DJ Backspin, compete in the costume contest, try your luck at the wine and whiskey pull, and more. Cost: $125 without costume | $100 with costume | members $10 off* *TWIF Members should call the front desk to purchase tickets, 978-443-1776.

Oktoberfest

Celebrate Oktoberfest with us at The Wayside Inn. Join us for a night of authentic German food, beer, and acoustic rock music with Hot Acoustics! Our annual Oktoberfest will be outside in our Event Tent. Tickets: $35 per person / $30 for TWIF members* $4 per beer during event Advance purchase required. Purchase through Resy, or by calling 978 443-1776. *TWIF members: call the Inn to receive special member rate, 978-443-1776. Menu: House-made Pickled Cucumbers Waldorf Salad Homemade Pretzel bites, with spicy mustard dipping sauce Grilled Bratwurst with caramelized onions Knockwurst, steamed in beer with sauerkraut Warm German Potato Salad “Hot Wings” with apple cider &amp; stout reduction Reiberdatschi, Braised Pork and Cabbage Käsespätzle (German cheesy noodles) Black Forest Cake and Apple Strudel German Apple Fritters, with cinnamon sugar and maple buttercream

Bites & Brews From Around the World

Longfellow’s Wayside Inn presents: Bites &amp; Brews From Around the World Friday, August 9, 2024 | 5:30pm – 9:00pm In the Wayside Inn Event Tent Cost: $30 per person / $25 TWIF members $4 per beer during the event Join us for an international beer and food tasting featuring specialties from six different countries. Enjoy live music by Steve Spector and Hot Acoustics. *TWIF members should call the front desk to purchase their ticket, 978-443-1776. Menu: Australia<ul><li>Foster's Beer</li><li>Blooming Onion Rings with BBQ sauce</li><li>Grilled Shrimp Skewers with vegetables</li><li>Prime Rib Burnt Ends</li></ul>Caribbean Islands<ul><li>Red Stripe Beer</li><li>Jerk Chicken Lollipops</li><li>Fried Plantain Chips with chile lime dressing</li></ul>Germany<ul><li>Weihenstephaner Beer</li><li>Beer-braised Bratwurst with caramelized onions</li><li>House-made Pretzels with beer cheese fondu</li><li>Reiberdatschi - German-style potato cakes with sauerkraut and pork</li><li>German Bread Pudding</li></ul>Ireland<ul><li>Guinness</li><li>Irish Deviled Eggs with roast beef hash and spicy mustard</li><li>Irish Soda Bread with molasses butter</li></ul>Italy<ul><li>Peroni Beer</li><li>Bruschetta with nut free pesto, cherry tomatoes, and mozzarella</li><li>Sicilian Eggplant Caponata</li><li>Fried Olives stuffed with gorgonzola cheese</li><li>Assorted Cannolis</li></ul>Mexico<ul><li>Modelo Beer</li><li>Mini Chili Rellenos with spicy tomatoes, rice, and agave-tajin rub</li><li>Quesadillas with shrimp, Monterey Jack cheese, peppers, and onions</li><li>Street corn (Elote) with spicy aioli, cotija cheese, and tajin</li></ul>

Strawberry Concerts

In keeping with our Strawberry Concert tradition, we have 3 concerts scheduled in July: Tuesday, July 16: Quintessential Brass – Big Band Orchestra Tuesday, July 23: Catnip Junkies – New Orleans themed Tuesday, July 30: Southern Rail – Bluegrass Ticket prices: – for concert only: $20* – special concert dinner package: $50 (includes dinner, concert, strawberry shortcake, tax &amp; gratuity) *TWIF Members: Members receive $5 off concert or $10 off dinner package. Contributor members &amp; above receive complimentary admission for two (concert &amp; strawberry shortcake only) with their membership dues. Please call front desk to receive member tickets.

Finley's Adventures: A book talk with local author Sherry Fendell and her Labrador Retriever, Finley

Join The Wayside Inn Foundation in the Longfellow Memorial Garden of The Wayside Inn for a book talk with local author Sherry Fendell and her beloved Labrador Retriever, Finley. During the height of the COVID-19 pandemic in April 2020, Sherry and Finley found solace in the natural areas surrounding them. Together, they embarked on countless adventures, exploring the forests, fields, and beaches of New England. From May 2020 to May 2022, Sherry chronicled their escapades in a popular weekly newspaper column titled “Finley’s Adventures,” published in the Sudbury Town Crier. Sherry has woven these heartwarming tales into a book, with two of the stories set right here at the Wayside Inn Historic Site. Join us in the Longfellow Memorial Garden as Sherry shares selected readings from her book and delves into the inspiration behind her writing. This is a free event, and open to all! Signed copies of Sherry’s book will be available for purchase. Consider bringing a gently used book to donate to The Wayside Inn’s Free Little Library. About the Author: Sherry Fendell has lived in Sudbury, Massachusetts for 46 years. In addition to being a professional photographer and world traveler, she has dedicated thirty-five years to raising yellow Labrador Retrievers and has actively volunteered for Labrador Retriever Rescue for three years.

Longfellow Memorial Garden of The Wayside Inn

S22: conversations

Wondering what to do in Boston? Places to eat? Free activities? Good for a group? Date night spot? Girls night out? The best things to do? Ask Joyraft!

Best places to go in Boston? Things to do? Places to eat?

Questions & answers about things to do in Boston

Recs 💬

Community recs 💬

S4: top picks

The most fun, cool and unique things to do in Boston. Can’t miss events, shows and experiences. Concerts, restaurants, bars, free things in Boston and beyond.

The most fun and cool events happening around Boston

Hot and new things to do in Boston

Hot & new

Hot & new 🔥

S11: happening this weekend

What to do in Boston this weekend? From festivals, concerts, performances, free events, screenings and more, Joyraft has the best things to do in Boston.

25+ things to do in Boston/Cambridge/Somerville this weekend

Things to do in Boston this weekend

This wknd

This weekend for you

S21: roundups

Our top picks: outdoor dining, free events, spring festivals, best bars, upcoming concerts, museum parties - the latest in and around Boston.  Slug: joyraft-top-picks-best-things-to-do-boston-ma

Top picks of the best things to do in and around Boston

Joyraft picks: Boston’s best things to do

Roundups ⭐️

Curated by Joyraft ⭐️

S28: calendar experiences

This week in Boston

This week in Boston 📆

This week 📆

S20: c+d experiences

Discover new, unique events and experiences happening in and around Boston. Perfect for date night, good for a group or with a friend. Be the first to know.

The newest events happening in and around Boston

The newest events on Joyraft

Just added

Just added to Joyraft

S16: editor picks

The most unique and can’t miss things coming up in Boston / Cambridge / Somerville and beyond. Festivals, food, drinks, fairs, concerts, art and free activities.

Unique and Can’t Miss Things to Do in Boston

Can’t-miss things to do in Boston 🚨

Can't-miss things to do 🚨

S2 (A): top experiences

The most popular things to do on Joyraft. Concerts, restaurants, bars, events, parties, openings, kid friendly, date ideas, free things in Boston and beyond.

Top 20 things to do in Boston

Top 20: Joyraft’s most popular

Top 20

Top 20 on Joyraft

S3 (A): trending experiences

Discover can’t miss events and things to do in Boston. The most fun, unique and cool events coming to the Boston area this spring and summer.

The hottest events happening in Boston

Trending events on Joyraft

Trending 📈

S17: interest based

Your guide to everything free in and around Boston. From events, to fairs, to festivals, to outdoors. Joyraft has all the free events happening near you.

100+ free things to do in Boston and beyond

Free things to do in Boston

Free things to do

S19: interest based

Kid-friendly events in Boston

S18: interest based

Where to eat and drink in Boston? Joyraft has Boston’s newest bars, restaurants and specials. Drinks and pre fixe dinner menus. Cambridge & Somerville too.

Where

thewaysideinn

Experiences

Apple Fest 2025

Wayside 5k For Scholarships

Caymus Wine Dinner

Jaguar Club Road Show at The Wayside Inn

Roaring '20s Ball & Casino Night

Printing Press Demo with Andy Volpe

Historic 1700s Colonial Dinner

Historic 1700s Colonial Dinner

Fireside Chat with Paul Revere

Pre-St. Paddy's Day Luncheon

Jerusha's Halloween Ball

Oktoberfest

Bites & Brews From Around the World

Strawberry Concerts

Finley's Adventures: A book talk with local author Sherry Fendell and her Labrador Retriever, Finley