Okemo Valley Seasonal Guide 🍁🥾

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Special Events 🗓️

• Ludlow’s Oktoberfest by Johnny’s Kitchen – Oct 17
• Spooky Coaster & Glow-In-The-Dark Adventure – Oct 23, 24, 30, & 31
• Terra Italian Steakhouse – Wine Dinner – Oct 24
• Halloween on the Chester Green – Oct 31
•  Matilda’s Not-So-Scary Pet Costume Parade – Oct 31 
• Trunk or Treat at Benson’s Chevrolet – Oct 31 
• Halloween Party Feat. DJ JSPIN$ at Magic Mountain – Oct 31 
• Okemo Mountain School Ski & Snowboard Swap – Nov 20 – 22 
• Thanksgiving Dinner at The Grafton Inn – Nov 26
• William Raveis Annual Coat Drive – Oct 1 – Nov 30 

For more special events and fun things to do – visit our Events Calendar!

Outdoor Adventures

1. 🚵 Biking: Explore the many peaceful backroads in the region. Check out this guide. There are also plenty of mountain biking paths, including Okemo Valley Trails in Ludlow, Swoops & Loops at Ascutney, and Graton Trails and Outdoor Center.
2. 🥾 Walking & Hiking: Exploring the Okemo Valley wilderness on foot is easy thanks to the beautiful trail networks. Check out this list of hikes in the area!
3. 🥏 Disc Golf: Play a round of disc golf at Chester Pinnacle Recreation Area, Magic Mountain in Londonderry, & Jackson Gore in Ludlow.
4. 🚣‍♂️ Paddling: Get out your kayak, canoe, or paddleboard and go for a peaceful paddle on one of the many lakes in the region: Lowell Lake State Park in Londonderry, Gale Meadows Pond in Londonderry, Lake Ninevah in Mount Holly, Spring Lake in Shrewsberry, Woodward Reservoir in Plymouth, Echo Lake in Plymouth, plus Camp Plymouth State Park has boat rentals.
5. ⛳️ Golf: Enjoy the fresh greens and off-peak prices! Fox Run Golf Club & Crown Point Country Club are reopened for the season!
6. 🏊Swimming: Pick from rivers, lakes, ponds or pools; there are plenty of options for cooling off with a dip!
   1. Rivers: Buttermilk Falls (Ludlow), Rainbow Rock(Chester), Twenty Foot Hole(Reading), & Power Dam Recreation Area(Perkinsville)
   2. Lakes & Ponds: Camp Plymouth State Park, Stoughton Pond (Perkinsville), Weston Recreation Pond Pool & Woodward Reservoir (Plymouth)
   3. Pools: Spring House (Ludlow), Chester Municipal Pool, & Edgar May (Springfield)
7. 🎣 Fishing: Cast a line in the Black River or one of the MANY nearby lakes! Check out this resource for places to drop a hook.
8. 🐴 Horseback Riding: Enjoy a scenic ride through the countryside with local equestrian service, Mountain View Ranch.

Relaxation

1. 🧖  Enjoy a spa day + massage: Unwind with a spa day – visit the Castle Hill Resort and Spa. Indulge in a luxurious massage or soak in a hot tub. Visit Calm Moments Massage Studio and the unique herbal apothecary for a therapeutic massage at Thyme and Again Apothecary.
2. 🏞️ Scenic drives: Take a leisurely drive with the windows down through the valley to appreciate rolling mountains and fresh greenery. You’ll find lots of fun spots along the Route 100 Scenic Byway – bring a picnic!
3. 🏊 Swim & Fitness: Check out the Spring House Pool & Fitness Center schedule.

Shop, Stay, Play, and Dine in Okemo Valley
After a day of fun, a wide range of accommodations are available to suit every preference, from beautiful inns and charming bed-and-breakfasts to elegant hotels and luxurious resorts. Savor delicious dining options, whether you’re in the mood for a casual meal or a fine dining experience. From romantic candlelit dinners to family-friendly eateries, there’s something for everyone. (Browse Dining Guide Here). Additionally, find unique souvenirs and treasures while visiting local shops and exploring the arts & culture.

Whether you’re hiking through shaded glens, biking along the scenic Route 100 Byway, or browsing a farmers market in a historic village square, Okemo Valley is a celebration of connection—between people, place, and the beauty of the moment.

Thinking about a new home or a home away from home?
Discover the charm of Okemo Valley with our expert real estate partners! Whether you’re seeking a peaceful retreat for a weekend getaway, a short-term rental for seasonal adventures, or a forever home nestled in this picturesque region, our top guides are here to help.