Itineraries

Trip Ideas

Featured image for “Beer Holidays Worth Toasting: Celebrating September in Woodstock”
Beer

Beer Holidays Worth Toasting: Celebrating September in Woodstock

Featured image for “Apple-solutely Fall for Woodstock Orchards”
Apple Picking

Apple-solutely Fall for Woodstock Orchards

Featured image for “How to Throw the Cutest Picnic in Woodstock”
Featured

How to Throw the Cutest Picnic in Woodstock

Featured image for “Kid-Approved Adventures: Your Family’s Summer Day Trip to Woodstock, IL”
Family activities

Kid-Approved Adventures: Your Family’s Summer Day Trip to Woodstock, IL

Featured image for “Red, White & Woodstock: Your Weeklong Guide to the 4th”

Red, White & Woodstock: Your Weeklong Guide to the 4th

Featured image for “Weird & Wonderful Things in Woodstock: Part 2”
Featured

Weird & Wonderful Things in Woodstock: Part 2

Featured image for “Weird & Wonderful Things in Woodstock: Part 1”
Featured

Weird & Wonderful Things in Woodstock: Part 1

Featured image for “Celebrate National Margarita Day in Woodstock”
Drinks

Celebrate National Margarita Day in Woodstock

Featured image for “How to Spend Your Galentine’s Day in Woodstock”
Day Trip

How to Spend Your Galentine’s Day in Woodstock

Featured image for “Romantic Spots for a Cocktail in Woodstock, Illinois”
Date Night

Romantic Spots for a Cocktail in Woodstock, Illinois

Featured image for “Tips for Your First Groundhog Day in Woodstock, IL”
Groundhog Day

Tips for Your First Groundhog Day in Woodstock, IL

Featured image for “Reliving Movie Magic at the Cherry Tree Inn Bed & Breakfast in Woodstock, IL”
Groundhog Day

Reliving Movie Magic at the Cherry Tree Inn Bed & Breakfast in Woodstock, IL

Featured image for “Holiday Gift Shopping Guide for: The Child At Heart”
Holiday Shopping Gift Guide

Holiday Gift Shopping Guide for: The Child At Heart

Featured image for “Holiday Gift Shopping Guide for: The Hobbyist”
Holiday Shopping Gift Guide

Holiday Gift Shopping Guide for: The Hobbyist

Featured image for “Holiday Gift Shopping Guide for: The One-of-a-Kind and Handmade”
Holiday Shopping Gift Guide

Holiday Gift Shopping Guide for: The One-of-a-Kind and Handmade

Featured image for “Holiday Gift Shopping Guide for: The Home Decorator”
Holiday Shopping Gift Guide

Holiday Gift Shopping Guide for: The Home Decorator

Featured image for “Holiday Gift Shopping Guide for: The Vintage Lover”
Holiday Shopping Gift Guide

Holiday Gift Shopping Guide for: The Vintage Lover

Featured image for “Holiday Gift Shopping Guide for: The Fashionista”
Holiday Shopping Gift Guide

Holiday Gift Shopping Guide for: The Fashionista

Featured image for “Holiday Gift Shopping Guide for: The Bookworm”
Holiday Shopping Gift Guide

Holiday Gift Shopping Guide for: The Bookworm

Featured image for “Holiday Gift Shopping Guide for: The Foodie”
Holiday Shopping Gift Guide

Holiday Gift Shopping Guide for: The Foodie

Featured image for “Experience Holiday Magic at Woodstock Opera House”
Holidays

Experience Holiday Magic at Woodstock Opera House

Featured image for “Experience the Magic of Winter in Woodstock, Illinois: Holiday Lights, Festivities, and Local Charm”
Holidays

Experience the Magic of Winter in Woodstock, Illinois: Holiday Lights, Festivities, and Local Charm

Featured image for “Spend a Day in the Stars Hollow of Illinois”
Fall Weekend

Spend a Day in the Stars Hollow of Illinois

Featured image for “Discover All Seasons Orchard in Woodstock, Illinois”
Apple Picking

Discover All Seasons Orchard in Woodstock, Illinois

Featured image for “Discovering the Charm of Thrift and Vintage Shopping in Woodstock, Illinois”
Thrift Shopping

Discovering the Charm of Thrift and Vintage Shopping in Woodstock, Illinois

Featured image for “Discover the Charm of Woodstock, Illinois: Your Perfect Road Trip Destination”
Day Trip

Discover the Charm of Woodstock, Illinois: Your Perfect Road Trip Destination

Plan Your Trip