Schedule of Events

(All outdoor activities are weather permitting)

Friday, December 1, 5 – 8 pm

♦  Festive First Friday    5 – 8 pm
Shopkeepers and galleries welcome guests with light refreshments.
It’s the perfect time for some holiday shopping! Get your Passport (available in every store) for extra holiday savings!

  Horse-Drawn Carriage Rides     5 – 8 pm
A leisurely ride past historic homes. Carol singing encouraged!
Board carriages at Cross Street Realtors, 201 S. Cross Street

  Stories & Songs by the Fire     5 – 7 pm
300 Block of High Street

Local thespians Michele Volansky, Jamie Kirkpatrick, Andrew McCown, Melissa McGlynn,  and Jake Swane give voice to Christmas classics. Caroling by Kent School Carolers. Firepits will crackle merrily. Try S’mores, roasted chestnuts and hot chocolate or go for something with a little kick provided by Bad Alfred’s.

  Ornament Making     5 – 7:30 pm 
RiverArts Clay Studio, 204 High Street
Walk in and make an ornament for your tree! No reservations needed. You will use cookie cutters to make ornaments and paint them with underglazes. We’ll glaze, fire, and return them before Christmas (mail-shipment option for an additional $10).
$15 for 2 ornaments

300 Block of High Street
Alluring, professional, and jaw-droppingly talented, the ladies of Pyroxotic will offer a sizzling finale to First Friday Fire Pit fun!

Saturday, December 2, 10 am – 9 pm

  Holiday Farmers Market  8 am until Noon  •  Fountain Park
Christmas greens, crafts and fresh baked goods. An award-winning Chestertown tradition!

  Bells of the Bay Hand Bell Choir 
10:30 am, Fountain Park  •   2 pm, High Street

  Visit Santa    11 am – 1 pm  •  Fountain Park

  Carriage Rides         Noon – 3 pm  •  Historic District
A leisurely ride past historic buildings and homes. Board carriages at Cross Street Realtors, 201 S. Cross Street

  Ornament Making     10:30 am – 4 pm  
RiverArts Clay Studio, 204 High Street
Walk in and make an ornament for your tree! No reservations needed. Use cookie cutters to make ornaments and paint them with underglazes. We’ll glaze, fire, and return them before Christmas (mail-shipment option  for an additional $10).
$15 for 2 ornaments

  Book Talk: A Cratchit Family Christmas    11 am
The Book Plate,  112 S. Cross Street
What happened to all those beloved characters in the years after Scrooge’s miraculous transformation? Author Paul Mast tells us in his 2016 novel.  At this appearance, Paul will read from his book and sell and sign copies.

  Expert Talk: How “A Christmas Carol” Haunted Dickens     1 pm 
The Book Plate, 112 S. Cross Street
Katie Charles,
Washington College Professor of English
When Charles Dickens published A Christmas Carol in 1843, he little suspected that its blazing success would sentence him to producing a new hit Christmas book every year for the rest of his life. This talk places the beloved Christmas fable in the context of Dickens’s life and publishing career and examines the ways Dickens considered himself, like Scrooge, to be a haunted man.

  Holiday House Tour   1 – 4 pm
Pick up the map (which serves as your ticket) from the Dickens Welcome Center  (the former Chestertown Bank Building,  211 High Street) This walking tour will offer a peek inside seven of Chestertown’s finest Victorian and historic homes decked out in holiday finery. Refreshments and music included. Reservations required. Tickets: $20 in advance; $30 day of tour. PURCHASE TICKETS

   Jerry Brown “The Monkey Man” & Django 
Strolling 11 am – 5 pm
Magical minstrel Jerry Brown, a one-of-a-kind entertainer, plies the lost arts of a bygone era. His monkey pal, Django, will steal your heart away! Visit with Jerry and Django as they stroll, and catch his performances!
Two Shows: 11 am,  in front of Peoples Bank (weather permitting)
2 pm
, Dickens Welcome Center,  211 High Street

♦  The Peoples Sweet Shop     10 am – 3 pm
Peoples Bank, 100 Spring Avenue
The community bank transforms itself into a Victorian sweet shop with a display of handcrafted gingerbread houses by bank staff, family and friends.

  Children’s Games     10 am –  4 pm  •  Courthouse Lawn
Try the games that Victorian children played! The Victorians are credited with ‘inventing childhood’, through their efforts to stop child labor and the introduction of compulsory education. But today, we play!

  Watch out for the Wheelmen!     11 am – 2 pm
Members of The Wheelman antique bicycle club will pedal by aboard their big-wheeled machines.

  Walking Christmas Tree   1 – 4 pm
Make a donation to the Kent County Food Pantry and hang an ornament on the branches.

  High Tea & Scones   3 – 5 pm
Hynson-Ringgold House,
106 South Water Street
$35, Reservations required
Relax by the fire in the historic home of Washington College’s president and enjoy a pot of tea with delectable sweet and savory treats. Finger sandwiches, scones and desserts served in old world elegance. Seating is limited. PURCHASE TICKETS

Sherry Salon with Neyah White       4 – 5:30 pm
236 Cannon Street (former Blue Heron Cafe)
$40. Reservations required  
A guided tasting of 6 different styles of Sherry, from bone-dry Manzanilla to dessert-sweet PX. We’ll talk history and production but mostly just enjoy the wines and learn about Sherry’s resurgence. Host Neyah White is a Chestertown native who has built a career in the drinks business. His longtime love of Sherry culminated in his winning the National Sherry Cocktail Competition in 2008. Seating is limited. PURCHASE TICKETS

  Beers & Bonfires      7 – 9 pm
Foot of High Street (weather location, 211 High Street, without the fire pits)

Bring friends and relax by the fire pits as you sample a selection of micro brewed Winter Ales. No reservations needed. Beers $5 each. Hosted in conjunction with the Kent County Chamber of Commerce Young Professionals

  Chester River Nightcap      8 – 9:30 pm
Aboard the Chester River Packet, Foot of High Street
Seating limited; reservations required.
$40 in advance, $50 at the door as space allows
The Royal Kent Gun and Whiskey Club & the River Packet invite you to join them for a Chester River Nightcap. You won’t actually be moving from the dock, but when you book “passage” you will receive:
• A tasting glass to take home
• Five wee drams of the Glenlivet range from the Founder’s Reserve all the way to the 21yr.
• A fine smoke from Ashton cigars
Bar open for business should you fall in love with any of the whiskies and want to buy a glass. Weather permitting, the upper deck of the Packet will be open for enjoying cigars.
PURCHASE TICKETS Please note: No dinner will be served, although small savory bites will accompany the tasting.

Fabulous food from vendors & restaurants

Bad Alfred’s Distillery    Friday, noon – 9 pm; Saturday, noon – 7 pm
323 High Street
English meat pies, Oyster pot pie, Dickens Gin Punch
Hot apple cider and gin punch under the tent on Friday night

Chester River Wine & Cheese    11 am – 2 pm
117 S. Cross Street
Ploughman’s Lunch: A traditional meal of bread, cheese and spirits for rural farm workers. Chester River kicks it up a notch and offers a Cheese board, meat/veggie hand pies plus a FREE wine and hard cider tasting. Guests may purchase non-alcohol cider. Hearty and delicious! In the festive garden behind the Cheese Shop on Cannon Street. $10 – $14. No reservations needed. Cheese boards to go all weekend.

White Swan Tavern      Noon – 4 pm
231 High Street
Front porch:  
Fresh shucked Oyster Bar by Orchard Point/Scott Budden, Crow Winery
Inside Tavern:
Special Children’s Tea, 1 pm;
Traditional tea served, 3 – 5 pm

The Kitchen at the Imperial      
208 High Street
A Dickens of a Menu!
Pear & Stilton Cheese Tart
Cornish Pasty  (Spiced beef, vegetables and herbs in puff pastry)
Roast Beef with Classic Yorkshire Pudding
Sticky Toffee Pudding
Reserve at 410-778-5000 ext. 1

Chester River Packet    6 – 8 pm
The foot of High Street
There is nothing more British than fish and chips. Freshly cooked, piping hot, smothered in salt, soused with vinegar, wrapped in newspaper and eaten out-of-doors on a cold and wintry day – it simply cannot be beat!

Barbara’s On the Bay
Scotch Eggs: Hard boiled egg, wrapped in sausage, dipped in breadcrumbs and baked. Served with Heavy Cream, Roasted Garlic, Dijon mustard and a touch of honey. A Brit tradition perfect for a brisk day!

Figgs Ordinary
207 Cross Street
Gluten-free Christmas puddings and other sweet and savory treats

Evergrain Bakery Cafe´
203 High Street

Scones and tea, coffee and pastries, pre-made sandwiches

The Fish Whistle
98 Cannon Street

Play It Again Sam
108 S. Cross Street
Coffee and Pastries


10 – 10:45 am (Fountain Park)  •   Belles of the Bay, Hand bell ensemble
10:45 – 11:30 am (High Street)  •   Tom McHugh & the Chester River Beggars
11:30 am – Noon (High Street)  •   Washington College Brass Ensemble
Noon – 1 pm (High Street)  •  Dovetail with Pres Harding, Jodie Littleton and Nevin Dawson
1 – 1:45 pm (High Street)  •  Tom McHugh & The Chester River Beggars
2:00 – 2:45 pm (High Street) • Bells of the Bay, Hand bell ensemble
3 – 4 pm (High Street)  •  Jigs & Reels

Strolling performers:
The Walking Musical Menagerie
Professor Jim Porter and Alexander Uskruaitis of Lost Northern Tribe

Sunday, December 3,  8 – 11 am

RUN LIKE THE DICKENS 5K    8 – 11 am
Route will start at High & Cross Streets
Costumes from A Christmas Carol are welcome. Included is a small jaunt through a local cemetery—will YOU spot one of the Christmas ghosts on your journey? Run like the Bobbies are after you! Benefits the Kent County Community Food Pantry. Advance registration: $30 race fee + $2.50 sign up fee.  Day off registration: $35 + $3 sign up fee. REGISTER

DICKENS DASH Kids Run    9 – 11 am
High Street and Lawyers Row

Children are encouraged to hotfoot it at The Dickens Dash. Kids 12 and under. Free

Plenty of parking at Wilmer Park and at the Kent County Courthouse