Crowds enjoying the Scotland CT Highland Games festival in Scotland, Connecticut, during fall.

House Hunting Around the Scotland CT Highland Games in Windham County

September 28, 20255 min read

Introduction

House hunting in Windham County, Connecticut, is even more exciting when paired with a local tradition like the Scotland CT Highland Games. Did you know these games have been bringing the community together with Scottish music, athletics, and food for nearly 40 years?

In this guide, I’ll show you how to make the most of the Highland Games weekend while exploring nearby homes for sale. From places to stay, to the best eats, to touring neighborhoods, you’ll get a full insider’s look at life in Windham County.

Hi, I’m Melinda, an AI-Certified Realtor® serving Tolland, Windham, Hartford, New London, and Middlesex counties. I love helping my clients not just find homes, but discover the lifestyle that comes with each community. Let’s explore Windham County together 🏡✨.


Where are the Scotland CT Highland Games located?

The Scotland CT Highland Games are held every October at the Walgreens Farm in Scotland, Connecticut, in Windham County. This annual event brings together Scottish traditions like bagpipes, caber tosses, and Highland dancing.

Being right in the heart of Windham County makes the Games a perfect backdrop for house hunters—while you enjoy the event, you’re also experiencing the charm of the surrounding neighborhoods. According to Visit Connecticut, Windham County is one of the state’s hidden gems, filled with rolling hills, historic villages, and affordable housing opportunities (https://www.ctvisit.com).


Where should you stay when house hunting in Windham County?

If you’re planning a weekend of house hunting around the Highland Games, you’ll want a cozy place to stay nearby. Popular choices include:

  • Local B&Bs like Scotland Historical Inn for small-town charm.

  • Airbnbs and vacation rentals in Windham or Norwich for flexible stays.

  • Hotels in Willimantic or Norwich, offering convenient access to restaurants and shops.

Staying local gives you a chance to “test drive” the community, see what daily life feels like, and shorten your drive when touring homes. According to Realtor.com, staying overnight in an area you’re considering moving to can give valuable perspective (https://www.realtor.com).


What are the best places to eat near the Highland Games?

Food is a huge part of the Highland Games experience, but don’t miss out on nearby local gems:

  • Celtic food vendors at the Games serving haggis, fish and chips, and meat pies.

  • Willimantic Brewing Company – a local favorite for craft beers and hearty meals.

  • That Breakfast Place in Norwich – a cozy spot perfect before a day of touring homes.

  • Mañana Mexican Restaurant in Windham – a casual choice for families.

Eating where the locals eat gives you a feel for the community vibe, which is just as important as seeing houses.


Can you tour homes while attending the Highland Games?

Yes, house hunting can fit right into your Highland Games weekend! I often schedule showings for out-of-town clients who come to events like this—it’s the perfect way to combine fun with a serious home search.

Homes in Windham County range from historic Colonials in towns like Scotland and Hampton, to newer builds in Plainfield and Willimantic. According to Zillow, the median home price in Windham County is still more affordable than much of Connecticut, making it attractive for buyers (https://www.zillow.com).

So while you’re enjoying bagpipes and caber tosses, you could also be stepping into your future dream home.


What makes Windham County a great place to live?

Windham County offers a mix of small-town charm and access to larger cities like Hartford and Norwich. You’ll find:

  • Affordable homes compared to coastal CT counties.

  • Rich history with 18th and 19th-century homes still standing.

  • Community spirit, highlighted by events like the Highland Games.

  • Nature access, including hiking trails, rivers, and state parks.

According to the National Association of Realtors, lifestyle amenities and community events play a big role in how buyers choose where to live (https://www.nar.realtor).


Why work with an AI-Certified Realtor® in Connecticut?

As an AI-Certified Realtor®, I use technology to make your home search smoother, faster, and more successful. Here’s how my AI tools help you:

  • 📍 Pinpoint homes that fit your lifestyle faster.

  • 📸 Market listings with precision, reaching the right buyers.

  • Save you time by automating background searches.

  • 💰 Attract more offers with smarter marketing campaigns.

Of course, I pair AI with my personal knowledge of Connecticut neighborhoods. Technology works best when guided by a Realtor® who truly understands the local market.


Conclusion

House hunting in Windham County doesn’t have to be stressful—it can actually be fun when you tie it to a beloved local event like the Scotland CT Highland Games. You’ll get a taste of community life, explore local eats, and see firsthand the neighborhoods you may soon call home.

Call me at 860-985-4363 or visit melindatherealtor.com for a free consultation. Never too busy for you to be my #1 client.


Frequently Asked Questions

Q: When are the Scotland CT Highland Games held?
A: They are held annually in October at Walgreen’s Farm in Scotland, CT, and attract thousands of visitors from across New England.

Q: What types of homes are common in Windham County?
A: You’ll find Colonials, farmhouses, and newer builds. Many homes here feature larger lots compared to other Connecticut counties.

Q: Is Windham County affordable compared to other CT areas?
A: Yes, home prices here are generally more affordable than in Fairfield or New Haven counties, making it a great entry point for buyers.

Q: Can I tour homes the same weekend as the Highland Games?
A: Absolutely! I often schedule tours for clients attending local events, making it a perfect way to combine fun and house hunting.

Q: What’s the commute like from Windham County to Hartford?
A: The average drive is about 45 minutes to an hour, making it manageable for those who work in the city but want country living.


Sources

  1. Visit Connecticut – https://www.ctvisit.com

  2. Realtor.comhttps://www.realtor.com

  3. Zillow – https://www.zillow.com

  4. National Association of Realtors – https://www.nar.realtor

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