Travel Destinations

North America Travel

Chestertown maryland

Discover Pinterest’s best ideas and inspiration for Chestertown maryland. Get inspired and try out new things.

148 people searched this

·

Last updated 6d

Chestertown Maryland, Visit Maryland, Pennsylvania Travel, Eastern Shore Maryland, Colonial Williamsburg, Wine Cheese, Eastern Shore, Chesapeake Bay, Trip Ideas

Chestertown Maryland

Pennsylvania Travel

Eastern Shore Maryland

Colonial Williamsburg

City Guide: How to Spend a Weekend in Chestertown - Washingtonian

Where to Eat 1. Chester River Wine & Cheese Pick out your picnic provisions—imported cheeses, salamis, antipasti, and bottles of wine—from this gourmet shop and spread a blanket by the river. Don’t forget a scoop of gelato for dessert. 117 S. Cross St.; 443-282-0220. 2. Evergrain Bread Co. Since opening shop in 2010, owner/baker Douglas

68

Chestertown Maryland, Downtown Shopping, Victorian Manor, Victorian House Plans, Unique Architecture, Pink Lady, Manor House, Woman Painting, Historic Homes

Chestertown Maryland

Downtown Shopping

Victorian Manor

Victorian House Plans

Unique Architecture

125 Washington Ave, Chestertown, MD 21620 | realtor.com®

View detailed information about property 125 Washington Ave, Chestertown, MD 21620 including listing details, property photos, school and neighborhood data, and much more.

16

Chestertown, Maryland, has a fascinating history. Combined with great food, drink, and lodging, Chestertown is a must-see when you visit Maryland. Read on for why you need to explore Chestertown, MD. Chestertown Maryland, Visit Maryland, Delmarva Peninsula, Travel Recommendations, Great Food, Weekend Trips, Walking Tour, Small Town, Weekend Getaways

Chestertown Maryland

Delmarva Peninsula

Travel Recommendations

Weekend Getaways

Explore Chestertown, Maryland: Small Town, Big Fun

Chestertown, Maryland, has a fascinating history. Combined with great food, drink, and lodging, Chestertown is a must-see when you visit Maryland. Read on for why you need to explore Chestertown, MD.

15

Town of Chestertown MD | Small-Town Escapes: Chestertown, MD | Garden and Gun Chestertown Maryland, Delmarva Peninsula, Eastern Shore Maryland, Safe Harbor, Eastern Shore, Chesapeake Bay, New Town, Summer Nights, Country Life

Chestertown Maryland

Delmarva Peninsula

Eastern Shore Maryland

Small-Town Escapes: Chestertown, MD

Colonial splendor and creative energy on the Chesapeake Bay

48

c. 1730 Federal For Sale in Chestertown, Maryland - OldHouses.com Federal Architecture, Federal House, Chestertown Maryland, Washington College, Fountain Park, Brick Floor, Brick Path, Dining Room Fireplace, Wood Floors Wide Plank

Federal Architecture

Chestertown Maryland

Washington College

Dining Room Fireplace

Wood Floors Wide Plank

c. 1730 Federal Sold in Chestertown, Maryland

GEDDES PIPER HOUSE * Stately, brick Federal, ca.1730, residence is in FINE preserved condition. * Architecturally pure. * Upon entering, one experiences the serenity. * Situated on quiet street in heart of Chestertown’s Historic District. * One full bath. Opportunities for more. * Four plus bedrooms. * High ceilings. Handsome 18c. woodwork, trim & hardware. * Original random width pine floors. * Twelve over twelve original windows. * Inviting entrance hall with…

5

#easternshore #maryland #chestertown #summerstyle #smalltownromance #college Washington College Chestertown, Washington College, Small Town Romance, Eastern Shore, College Life, Trip Planning, Maryland, Washington, Back To School

Washington College Chestertown

Washington College

Small Town Romance

Washington college

#easternshore #maryland #chestertown #summerstyle #smalltownromance #college

7

Chestertown Maryland, Pennsylvania Travel, Eastern Shore, Best Dining, Blue Heron, Restaurant Review, Best Restaurants, Travel Ideas, Personal Finance

Chestertown Maryland

Pennsylvania Travel

Restaurant Review

Best Restaurants

Personal Finance

THE 10 BEST Restaurants in Chestertown (Updated January 2025)

Best Dining in Chestertown, Maryland: See 1,357 Tripadvisor traveler reviews of 38 Chestertown restaurants and search by cuisine, price, location, and more.

12

A collage featuring charming Maryland scenes, including historic brick streets, bustling outdoor dining, a serene waterfront with sailboats, and quaint shops, some of the best places to live in Maryland. Leonardtown Maryland, Maryland Homes, Westminster Maryland, Places To Live, 2025 Vision, Baltimore Maryland, Best Places To Live, Quality Of Life, Best Cities

Leonardtown Maryland

Westminster Maryland

Baltimore Maryland

Best Places To Live

Quality Of Life

12 Best Places to Live in Maryland

The best places to live in Maryland include Annapolis, Baltimore, and more. Here's a round-up of places to live in MD.

5

10 Best Fall Trips in Maryland Fall In Maryland, What To Do In Maryland, Things To Do In Maryland In Fall, Fun Things To Do In Maryland, Maryland Things To Do, Maryland Bucket List, Maryland Aesthetic, Things To Do In Maryland, Maryland Day Trips

Fall In Maryland

What To Do In Maryland

Things To Do In Maryland In Fall

Fun Things To Do In Maryland

Maryland Things To Do

Maryland Bucket List

Maryland Aesthetic

Things To Do In Maryland

Maryland Day Trips

10 Best Fall Trips in Maryland

10 Best Fall Trips in Maryland | maryland fall foliage | maryland bucket list road trips | things to do in maryland in fall | maryland fall activities | maryland travel bucket lists | places to travel in maryland | maryland travel guide | maryland travel tips | maryland travel | fall bucket list #fall #maryland #usa #travel

87

c. 1760 Colonial For Sale in Chestertown, Maryland - OldHouses.com Curved Stairway, Brick Garage, Chestertown Maryland, Kitchen Color Scheme, Brick Driveway, Chesapeake Bay Bridge, Vibrant Kitchen, Landscape Mural, Grand Entry

Curved Stairway

Chestertown Maryland

Kitchen Color Scheme

Chesapeake Bay Bridge

Vibrant Kitchen

Landscape Mural

c. 1760 Colonial For Sale in Chestertown, Maryland

A Landmark Property on the Chester River This exceptional property is a rare find for two important reasons. First, because of its deep and rich history of the County of Kent prominent families who built and lived there. Secondly, because rarely does one find an 18th c. building in such very fine condition so sensitively restored and brought in 21st c. The present owner spent two-years restoring this worthy treasure beginning by restoring its structural integrity and then adding a new…

3

Related interests

Baltimore Maryland Aesthetic

Provincetown Massachusetts

Marblehead Massachusetts

Annapolis Maryland

Ocean City Maryland Aesthetic

Downtown Chicago

Frederick Maryland

Worcester Massachusetts

Virginia Gardner

Chestertown Maryland