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Breaking Out Of The Concrete Jungle With Fall Getaways

Bear Mountain Foliage. Courtesy of Kerry Botensten.

By Kerry Botensten

Summer isn’t the only time to get out of town! Share houses closing means the beginning of drinking craft beers and exploring castles. In the fall, beaches turn to mountains as New Yorkers start heading north to the Hudson Valley, one of the best fall foliage viewing spots (according to me). With notably one of the best transportation systems in the world, it’s easy to escape to many great places. For the novice Hudson Valley travelers, the 3 B’s are a good benchmark for a weekend getaway: Beacon, Bannerman Island and Bear Mountain.  See the foliage in Dutchess County from all views: an island, a town and a mountain.  

Starting at Grand Central Station, hop on the Hudson Line heading north. A short 60 minute train ride from the concrete jungle to Bear Mountain will cure your need for the outdoors. This NY state park includes boating, fishing, biking/hiking trails, a seasonal pool and an epic destination for fall foliage viewing. A moderate two mile hike up from the base to Perkins Tower will not disappoint. At the top, on a clear day, you can catch a glimpse of the “The City”.  Especially in the fall, I vote this as the best view of the Manhattan skyline. Not only is the hike and view breathtaking, but the trail itself is historic. 

Bear Mountain Hike. Courtesy of Kerry Botensten.

Bear Mountain is part of the Appalachian Trail, the longest marked footpath in the nation, spanning over 2,200 miles from Maine to Georgia and across 14 states. In iPhone terms, that’s about 5 million steps! But, if you don’t have 5-7 months available to hike the full trail, then this is the next best way to be a part of it! In fact, Bear Mountain was the first starting point of the trail in 1923. If this hiking talk is exhausting you, I’ll let you in on a little secret…you can actually drive to the top of Bear Mountain and skip the hike. Shhhhhh! 

When you’re done, head to the historic Bear Mountain Inn at the base of the mountain. The second floor restaurant opens up into vaulted ceilings, stone walls, an oversized fireplace and views of Hessian Lake. It’s the perfect spot for resting your tired feet and sipping hot chocolate. If you fancy spending the night (or having a wedding there), no problem! It has 63 rooms to choose from, including a few pet friendly ones!

If you’d rather leave your hiking shoes at home, head 30 minutes further on the Metro North to Beacon. The Metro North train disembarks next to the Hudson Long Dock Park, which sits on the Hudson River with a majestic view of the river and Newburgh. It’s home to picnic spots, fishing, and kayaking. It’s also one of two departure areas to visit Pollepel Island, home of Bannerman Castle, also known as the Castle on the Hudson. The title “castle” is a bit deceiving since it was never actually used as a castle, but instead as a military fortress to store weapons. It’s a quick scenic boat ride or a tough kayak ride from shore, but only accessible via approved tours during the warmer months. History lovers and photographers will revel in the scenic boat ride over and the colorful fall views from the top of the 6.5 acre island.  

Bannerman Castle. Courtesy of Kerry Botensten.

Once you return to shore, venture into this unique upstate town. Beacon is the happy marriage of colonial America and hipster Brooklyn! Craft breweries, art galleries, farm to table restaurants, and American flags line the old town streets. Views of the Hudson River and the autumn colored trees in the Hudson Highlands can be seen from both ends of the picturesque town. It’s packed with something for everyone, but mostly known for the chill vibe of its breweries. Stroll to the end of Main Street or get there quicker via the The Beacon Free Loop, a free shuttle area town. 

At the end, near Fishkill Creek, you’ll spot a nondescript white warehouse with food trucks (“pop up kitchens”) outside. This is the Hudson Valley Brewery, started by an ex Hollywood guy who came back to his roots in the Hudson Valley. The casual vibe of the open air high ceilings picnic benches, and colorful beer cans make this tap room a fun spot for groups. Try the local sour IPA to get a feel for what the locals like. When the sun goes down, the outside deck is lit with streaming lights to keep the momentum going.

Up the block is 2 Way Brewing Company with a more artsy vibe. This brewery is adorned with eclectic trinkets, chalkboard beer menus and a guest graffitied bar top. Board games on the patio, beer flights and hosted trivia night makes the venue ideal for mingling. The Texas BBQ inspired menu and friendly bartenders sets it apart from the rest and worth the visit.  Don’t forget to examine and ask them about the walls near the bathroom. Music lovers can head over to the Towne Crier Cafe for nightly live music, open mic night and the famous Sunday brunch. It’s been a Beacon staple for over 30 years and still gets packed!

Bear Mountain Inn. Courtesy of Kerry Botensten.

There are also plenty of spot for foodies, but the Kitchen Sink is my go-to restaurant. Mostly because I never know what will be on the menu! It’s all local fresh farm produce, but prepared in unusual ways…think butternut squash lasagna. The menu changes weekly, based on seasonal crops and the mood of the chef. You’ll also feel right at home on the back patio which will resemble your neighbor’s patio on a summer holiday. Getting a seat may take awhile but it’s worth it.

If you want to see Beacon in full swing, visit for the monthly Second Saturdays for the city wide event. Hopefully, I don’t need to mention when it is. Until 9pm, the city center is booming with art gallery openings, local food tastings and music – which leaves plenty of time to take the 10pm train back to Manhattan.  

That’s how you break out of the concrete jungle for a chill autumn weekend. Cheers to more weekend exploring!

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