Group Tours in Caroline County

Stunning landscapes, outdoor adventures, heritage experiences & small town charm…

Located on the Eastern Shore of the Chesapeake Bay and bisected by the Choptank River, Caroline County is a rural haven of agriculture, historic landscapes, and outdoor recreation. Less than two hours from Baltimore, Philadelphia, and Washington, D.C., it’s is the perfect destination for history buffs, nature lovers, and those seeking a quiet getaway.

Here you’ll find a relaxing lifestyle where you can retrace Underground Railroad pathways and visit captivating settings. Enjoy Caroline’s wealth of historic sites, nature preserves and parks, winding waterways, scenic countryside, and dining options.

Download our Group Tour Profile sheet here, or check out our sampling of group tour attractions below.


The Chesapeake Culinary Center offers cooking classes and catered lunches to groups of all sizes! They are also home to Shore Gourmet, a market and cafe that offers Maryland-made specialty products.

Faulkner Branch Cidery & Distilling Co. is a local distilling company that utilizes fruit grown from the on-site Blades Orchard. Explore their market or sample cider in their tasting room.

Harvest Ridge Winery offers wine tours and tastings to groups of all sizes.

Steve Konopelski, Patissier of Turnbridge Point, a waterfront B&B, offers cooking classes, catering, high tea and more. Chef Steve was a finalist on Food Network’s Holiday Baking Championship and is renowned for his pastries, cakes and culinary creations.


The Harriet Tubman Underground Railroad Byway highlights the stories of Harriet Tubman, the Underground Railroad, freedom seekers and abolitionists. Stops include the James H. Webb Cabin, the Linchester Mill, Tuckahoe Neck Meeting House, the Caroline Courthouse Green and more.

The Museum of Rural Life in Denton highlights Caroline County’s rich agrarian history and includes portions of four historic houses.

The Linchester Mill was one of the last water-powered mills on the Eastern Shore. The campus features the mill, miller’s dwelling, Hog Island School, Hunting Creek, a nature trail and guided tours by appointment.

The Choptank River Heritage Center, housed in a turn of the century steamboat warehouse, tells the story of the heritage of this commercial and cultural trade Mecca.


FACES (Fiber Arts Center of the Eastern Shore), is a destination for the area’s many quilt and fiber art enthusiasts. View works by fiber artists from the Delmarva Peninsula.

The Foundry is an art gallery and gift shop featuring the work of more than 40 local artists.


Adkins Arboretum is a 400-acre garden and preserve with pathways that meander through native woodlands, meadows, streams and wetlands. Offerings include a visitor center, gift shop and gallery.

Schrader’s Bridgetown Manor features a 24-station sporting clay course, 25,000 acres of prime hunting property, certified instruction and a charming Bed & Breakfast.

Have an agritourism adventure at Outstanding Dreams Farm or Tuckahoe Treasures, two of Caroline County’s alpaca farms! Tour the farms, browse through their unique gift shops and meet the alpacas!


There are many unique shopping experiences in Caroline County. Find a treasure at one of our many antique stores, stroll through the shops in our charming downtowns or bring home farm fresh produce from our many farm stands, including local-favorite Clayton Farms.

Contact us to help plan your tour at 410.479.0655 or

Denton Rod & Tackle

September 18, 2021

Farm Markets, Produce Stands & U-Pick Produce

August 18, 2020

Civil War Trail

January 24, 2020

Holiday Park

January 19, 2020

Martinak State Park

January 14, 2020

Retreat House

January 9, 2020

Schrader’s Bridgetown Manor

January 8, 2020

Tuckahoe State Park

January 7, 2020

Night Kitchen Coffee

December 2, 2019

JZ Farms

October 1, 2019

Preston Historical Society Museum

August 2, 2018

Federal Brewing Company

July 8, 2018

Smokey Cat Lavender Farm

May 29, 2018

Caroline County 4-H Park

February 7, 2018

Work Horse Farm Rescue & Exotics

January 18, 2018

James H. Webb Log Cabin

January 18, 2018

Ridgely Telephone Exchange Museum

January 18, 2018

Museum of Rural Life

January 18, 2018

Linchester Mill

January 18, 2018

Greensboro Visitors Gallery

January 18, 2018

Greensboro Museum

January 18, 2018

Federalsburg Area Heritage Museum

January 18, 2018


January 18, 2018

Paddlefest on the Choptank

Northern Choptank Adventures

January 18, 2018

River Run Cruises

January 18, 2018

Delmarva Balloon Rides

January 18, 2018

Cycling in Caroline

January 18, 2018

Caroline County Shooting Preserve

January 18, 2018

The Foundry

January 18, 2018

Tuckahoe Treasures Alpaca Farm

January 18, 2018

Shore Good Heritage Farm

January 18, 2018

Outstanding Dreams Alpaca Farm

January 18, 2018

Jewel’s Landing Farm

January 18, 2018

Chincoteague Pony Rescue

January 18, 2018

Harvest Ridge Winery

January 18, 2018

Faulkner Branch Cidery

January 18, 2018

Idylwild Wildlife Management Area

January 18, 2018

Public Landings

January 18, 2018

Marinas & Boat Ramps

January 18, 2018