Eastern Shore Halloween Happenings

Halloween Happenings
Saturday, October 24
Thompson Park, Easton
10 a.m.
In the event of rain, the event is held at the Avalon Theatre


Held annually on the Saturday before Halloween, this event is a double-header. At 10am in the morning, young children (encouraged to be in costume) gather in Thompson Park for games, entertainment and prizes for costumes. They are then led around the block (from Washington to Goldsborough to Harrison, and back to Thompson Park) in a fun, costumed parade of Trick or Treaters, to get candy from downtown merchants. (In the event of rain, the event is held in the Avalon Theatre.) Free

The St. Michaels Great Pumpkin Festival
Saturday, October 24– Sunday, October 25
Various locations throughout St. Michaels
St. Michaels Business Association


October 24 & 25 – The Great Pumpkin Festival – The town of St. Michaels comes alive with the celebration of pumpkins with a weekend of activities for everyone to enjoy.

Sat., Oct. 24th

8:30 a.m. – Registration for the 5K walk/run at St. Michaels Elementary, sponsored by the St. Michaels Sports Boosters.

9:00 a.m. – Start of the 5K walk/run from St. Michaels Elementary.

8:30 a.m. – Master Carvers begin work on the massive gourds. Public is welcome to observe the Pumpkin Carving Contest in progress from 8:30 a.m.–12:30 p.m. at Christ Church Etherton Hall. Judging will take place between 12:30 and 1:30 p.m. The gallery of carved creations will be open to the public from 1:30–7:00 p.m. at Christ Church.

9:00–10:00 a.m. – Professional and Amateur Chefs enter their culinary creations for the Pumpkin Pie Competition at Christ Church Etherton Hall. Judging takes place between 10:00 and 11:00 a.m. Pies and other seasonal baked goods and beverages go on sale at 11:00 am.

10:30 a.m. – Pit Beef Sale at St. Luke’s Church parking lot for benefit of the St. Michaels Sports Boosters.

1:00–4:00 p.m. – St. Luke’s Children’s Pumpkin Patch – a myriad of games and treats for children at St. Luke’s Parish Hall, including pumpkin decorating, face painting, apple bobbing and much more. Snacks and beverages will also be available for a small fee.

2:00–4:00 p.m. – St. Michaels High School Street Carvers – enjoy the creativity of these teens as they transform giant pumpkins into works of art before your very eyes.

8:00 p.m. – Just east of the gates of St. Luke’s cemetery, prepare to be thrilled by the outdoor showing of the original “Phantom of the Opera” on a big screen, under the harvest moon. Chairs will be available but you’re welcome to bring lawn chairs or your own refreshments. The presentation is free and open to the public. Popcorn and beverages are available for a small fee.

GHOST TOURS will be available with Kelly Cox throughout this weekend and the following weekend. Beginning at the Visitors Center at the intersection of Mill and Talbot Streets at 8:00 pm and 9:00 pm. $10 per person

Sunday, Oct. 25

9:00 a.m. registration – Jack Russell Terrier Races & Dachshund Dash at the Inn At Perry Cabin. Races start at 11:00. Sponsored by the Jack Russell Terrier Race Committee.

3:00 p.m. – C Street’s Fireman’s Auction at Carpenter Street Saloon.

October FunFest for Kids of All Ages
Saturday, October 24
Christ United Methodist Church, Chestertown
3-5 p.m.


A not-to-be-missed October FunFest features a costume parade and many games. Activities include such favorites as Ring Toss, Eat a Donut Off the String, Twister, Bean Bag Throw, and Ghost Darts. Prizes, apple cider, cookies, popcorn, and lots of fun! Call Nancy Harrington (410-928-3273) or Darryl and Lucia Calloway (410-928-3883) for information.

Historic Stevensville Family Fall Festival––Artoberfest
Saturday, October 24
9 a.m.-4 p.m.

KIFA 410-643-7424

Enjoy artists, artisans, food, family activities, a beer garden, and live entertainment.