Winchester, New Hampshire

Embark on a picturesque journey along the Ashuelot River, savor a charming visit to Draft Gratitude, or experience the winding trails of Pisgah State Park. Winchester is calling you to uncover the hidden gems of New Hampshire’s Monadnock Region. Choose your adventure and discover Winchester in the southwest corner of New Hampshire.

 

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Main Street Winchester

Winchester’s town offices are located in a pretty building along the Main Street. It sets the tone for the town, a sense of simplicity, character, history, and uniqueness. New England Sweetwater Farm & Distillery and a handful of small businesses also line the road. During the summer months, be sure to explore the seasonal farmers market off Main Street where you can find fresh produce and handmade crafts, showcasing the talents of the community.

Winchester is famous for its annual Pickle Festival! I have it on my wish list for 2025 and expect to dedicate a separate post to it. As you can imagine, you can expect all things pickle including a pickle eating contest! Parades, crafts, music, food, and more round out this great community event.

Winchester, NH

Winchester, NH

Winchester, NH

 

The Ashuelot River

Winchester is a town that beautifully embraces the Ashuelot River, a captivating waterway that begins its journey in Washington, New Hampshire. This river gracefully flows through the charming towns and cities of the Monadnock Region, ultimately merging with the Connecticut River in Hinsdale.

If you’re in search of a breathtaking drive, make sure to add Route 63 to your itinerary. This scenic route is a delight in every season, but the vibrant spring waters and the stunning autumn colors are truly unforgettable.

The area is also dotted with amazing historic covered bridges. The Coombs Covered Bridge and the gorgeous Ashuelot Covered Bridge are a must for anyone who loves and appreciates these works of art.

Winchester, NH

My youngest daughter and I paddled the Ashuelot from Keene to Winchester some years ago and it was an amazing treat to travel under the many covered bridges in Swanzey and Winchester.

Winchester, NH

 

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Pisgah State Park

The NH Division of Forests and Lands provides fantastic insights into the rich history and scenic trails of Pisgah. If you’re planning a hike, be sure to check out Friends of Pisgah (FOP) as an invaluable resource. Did you know that Pisgah State Park is the largest state park in New Hampshire?

I’ve enjoyed many hikes starting from the Kilburn Trailhead in Chesterfield, and Winchester’s Old Chesterfield Rd. trailhead is next on my list! Pisgah is a hidden gem in the Monadnock Region, and it certainly deserves a dedicated post in the future.

Winchester, NH

Winchester, NH

Winchester, NH

 

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Draft Gratitude

Draft Gratitude is an extraordinary rescue operation you might easily miss as you drive past, but it deserves a visit. Conveniently located off Route 119, this non-profit is making a difference in the lives of draft horses and other animals.

Take a moment to watch their insightful short video that beautifully captures their mission and the passion behind their work. If you feel inspired, check out their website to discover how you can make a meaningful contribution through donations or by volunteering your time.

Winchester, NH

Winchester, NH

Winchester, NH

Winchester, NH

 

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Arlington Inn

Originally established in 1733, Winchester was known as Arlington. The Arlington Inn Tavern, a stunning building from 1810, underwent a thoughtful restoration starting in 2016, transforming it into a charming centerpiece on Winchester’s Main Street.

We have dined there multiple times and have always been impressed with the exceptional food and attentive service. Visit their website for more details on the Inn and available room accommodations.

Winchester, NH

Winchester, NH

Winchester, NH

Outlaw Brewing

Discovering Outlaw Kitchen & Brewing was a delightful surprise during our summer exploration of Winchester. Nestled on a picturesque property along Scotland Rd, this gem offers a great selection of food and craft brews.

With ample outdoor seating, you can soak in the stunning surroundings while enjoying occasional live music that adds to the atmosphere. Their smash burgers are out of this world! Be sure to visit the Outlaw Kitchen Facebook page to browse their enticing menu.

Winchester, NH

Winchester, NH

 

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Monadnock Speedway / Winchester Speedpark

If you’re a speed enthusiast, Winchester is the place to be. With the thrilling Monadnock Speedway and the exhilarating Winchester Speedpark, your need for speed will be fully satisfied. Both venues are conveniently located off Route 10.

Winchester Speedpark hosts the Motocross and Supercross series, while Monadnock Speedway features a quarter-mile track that supports the NASCAR Advance Auto Parts Weekly Series.

January doesn’t lend itself to pictures that do either venue justice. Both websites will give you a taste of the in-season racing vibes.

Winchester, NH

Winchester, NH

Shopping

Nestled in the heart of Winchester, a charming town with a population of just over five thousand, you’ll discover a delightful array of shopping options that cater to a surprising number of needs. From the friendly aisles of Kulicks, where you can find a little bit of everything, to Aubuchon Hardware, your go-to spot for all things home improvement, Winchester is impressive. Need outdoor equipment? Gary’s Power Equipment has you covered. For your pharmacy needs, Rite Aid is conveniently located, and don’t forget to swing by Dunkin’s for your favorite coffee and treats.

Winchester, NH Winchester, NH

Forest Lake and Campground

Forest Lake is home to Forest Lake Campground and Winchester’s town beach. The campground provides 150 sites with a mix of tent and trailer camping available.

Winchester, NH

Winchester, NH

Forest Lake is an important landmark within the town with its own sense of community. In July of 2023, torrential rains caused the dam that supports the lake to collapse. Since then, the community has worked very hard to reinforce and protect the lake from future problems. Check out this website and video dedicated to their efforts to repair and secure the dam and celebrate the sense of community within Winchester.

Is there a quaint town or city in New Hampshire that has always intrigued you but you haven’t had the chance to explore? I invite you to share your thoughts in the comments below. Who knows, it might just make its way onto my expanding list of must-visit places.

If you’re looking for more fun content that showcases the wonders of the Monadnock Region, don’t miss my post on The Dublin Gas Engine Meet.

Be sure to subscribe so you can stay updated on my next adventure. Each notice to subscribers includes a favorite picture from my latest post. And remember to like, follow, and share on social media!

Until we meet again, Live Free and Explore!

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