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Montgomery

Welcome to Montgomery, NY! This charming town in the Hudson Valley is known for its historic buildings, quaint shops, and friendly locals. Don't miss a visit to Angry Orchard for some delicious hard cider or a stroll through the picturesque Ward's Bridge Park. Montgomery is the perfect spot for a relaxing weekend getaway.

Recommendations

Eat$$$4.6/5

Ward's Bridge Inn

Nestled in the heart of Montgomery, Ward's Bridge Inn offers a charming ambiance, delectable cuisine, and rich local history, making it an iconic destination for a cozy meal and memorable gatherings.

Eat$$$4.5/5

wildfire grill

Wildfire Grill, located on Clinton Street in Montgomery, NY, offers a unique blend of mouthwatering barbecue and rustic ambiance, making it a must-visit destination for both locals and travelers seeking unforgettable flavors.

Eat$$$4.4/5

Copperfields Kildare Pub

At Copperfields Kildare Pub, guests can enjoy a vibrant atmosphere with hearty Irish fare, an impressive selection of craft brews, and live music, making it a beloved gathering spot in Montgomery.

Eat$$3.8/5

Dunkin'

At Dunkin', delight in a beloved array of fresh donuts and flavorful coffee, where the vibrant atmosphere and friendly service create the perfect stop for both locals and travelers in Montgomery, NY.

Stays

Stay4.35/5

The Borland Inn & Restaurant

Indulge in a cozy and charming bed and breakfast experience at The Borland Inn & Brunch House. Located in the heart of Montgomery, NY, this quaint spot offers delicious brunch options and a comfortable stay. Don't miss out on exploring the nearby historic sites and local shops during your stay!

Things To Do
Provided by

5/5

48 h

Private Hike/Wineries/Walkway Over the Hudson/1 night Hotel

The Walkway Over the Hudson is the longest and highest elevated pedestrian bridge in the world! Benmarl Winery is America's oldest Vineyard! When you accompany two of those facts with a cozy historic town to explore with a plentiful amount of restaurants, bars and eateries, you can't go wrong! Don't feel guilty indulging one bit, because you got some exercise in! Enjoy the famous Walkway Over the Hudson, a moderate to difficult level hike (easier options are available as well), gorgeous hotel accommodations for one night and 2 great local wineries! •the itinerary order is subject to change due to weather and the transportation mode used to arrive in the area. The itinerary change is always in the best interest of our guests. It may be needed (due to availability reasons) to visit different wineries than listed and/or stay at a different hotel.

$1,220.00

5/5

45 mins

45 Minute Scenic Horseback Trail Ride

Set against the backdrop of the breathtaking Hudson Valley (about an hour north of NYC), this 45-minute trail ride offers a unique opportunity to connect with nature on horseback. Accompanied by a skilled wrangler, riders will navigate through 117 acres of picturesque meadows, shaded woods, and a serene pond. No prior riding experience is necessary, as the skilled and friendly staff will ensure a safe and enjoyable ride. Keep an eye out for local wildlife as you traverse sunny fields. Suitable for ages 7 and up, this ride is perfect for families, friends, special events and celebrations, and beginners alike, promising a memorable adventure in the great outdoors with gentle horses. We also have a free petting zoo and offer pony rides for children 2 and up.

$95.00

5/5

Walkway Over the Hudson & Wineries- Private Transport

The Walkway Over the Hudson is the longest and highest elevated pedestrian bridge in the world! Benmarl Winery is America's oldest Vineyard! When you accompany two of those facts with a company that will bring you to and from your locations with professionalism, reliability and friendliness, you can't go wrong! Don't feel guilty indulging one bit at your wineries because you got some exercise in during your amazing time at the Walkway Over the Hudson! Optional bike rentals are available upon request for the Walkway Over the Hudson. Please let us know ahead of time. *Hotel accommodations are available upon request. Simply send us an email and we will be happy to assist you. *Depending on winery availability at the time of your booking, it may be necessary to visit different comparable local wineries than listed. *the Walkway Over the Hudson is a flat paved walkway that is 1.30 miles long. You will get picked up on the other side.

$235.00

4.2/5

2 h

2-Hour Small Group Central Park Bike Tour

Embark on a 2-hour journey around one of the world's most beautiful parks — a guided, 2-hour, small-group, Central Park bike tour. Explore its hidden secrets and enjoy the sites of Central Park — with personal service from a local, licensed tour guide. See the historic architecture, movie sites, gardens, hidden waterfalls, and much more. Along the way, learn about New York City's most-popular green space.

$119.00

4.1/5

LEGOLAND® New York Theme Park Admission Ticket

Discover endless family fun at LEGOLAND® New York Resort — the ultimate LEGO® theme park destination for kids ages 2–12! Located in the heart of the Hudson Valley, this unforgettable theme park invites families to ride, climb, splash, and build across seven immersive LEGO themed lands. Experience world exclusive attractions like the LEGO® Factory Adventure Ride, where you’ll transform into a Minifigure. Test your ninja skills on LEGO® NINJAGO® The Ride, embark on a medieval quest aboard the Dragon Coaster, and explore stunning miniature cities built entirely from LEGO bricks in MINILAND. Plus, don’t miss the all new LEGO Ferrari Build & Race experience, where kids can design, build, test, and race their own LEGO Ferrari on digital and physical tracks. From thrilling rides to hands on building adventures, awesome awaits at LEGOLAND New York! Experience the ultimate celebration of play during LEGO® Festival from July 20th to August 31!

$49.99

Hudson Valley Wineries- Private Transport- OR brewery/distillery

Benmarl Winery is America's oldest Vineyard! When you accompany that fact with a company that will bring you to and from your locations with professionalism, reliability and friendliness, you can't go wrong! We can't wait to book your reservations, make your itinerary, provide you with transportation (by us or one of our partnered transportation companies). You'll love all 3 of your winery stops for the day! Visit our website for more detailed information. Hotel accommodations are available upon request. Send us an email and we'll be happy to book you in a hotel or a private vacation rental (VRBO or Airbnb). Depending on availability, it may be necessary to visit different comparable local wineries than listed. Whichever winery we choose will also be enjoyable of course! We have lots of wineries in our area. We also can conduct your winery tour in other areas than what's listed such as Dutchess County, Ulster County, Columbia County and or Orange County. Email us for questions.

$235.00

45 mins

Date Night a 45 minutes Trail Ride

Your Date Night Experience Ride immerses you in the Hudson Valley’s natural beauty. Saddle up for a guided horseback trek through wooded trails, open fields, and blooming meadows, then pause for photo ops with your horse. After the ride, gather around a cozy fire pit on the lawn, where a curated charcuterie board, s’mores kit, and a choice of wine or sparkling cider await. Late‑afternoon rides reward you with a spectacular sunset over the barn. Ideal for couples, families, or groups celebrating birthdays, anniversaries, engagements, parties, Mother’s or Father’s Day, a memorable night out now!!

$160.00

Private Hudson Valley and Estate Tour from NYC with Transfer

Escape the city and uncork the Hudson Valley on a private wine tasting day trip from New York City. Roll through vineyard-draped hillsides and river-carved landscapes that define one of the Northeast's most beloved wine regions. At hand-picked Hudson Valley wineries, enjoy VIP tastings of small-batch, locally crafted wines while learning about the valley's thriving wine culture. Pass by grand historic estates that tell the story of the region's gilded past before pausing at a sweeping Hudson River viewpoint and soaking in scenery that stops you mid-sentence. Travel in comfort from start to finish with a knowledgeable guide bringing the story of New York wine country to life. -VIP tastings at select Hudson Valley wineries with locally sourced food pairings -Scenic Hudson River viewpoint stop - perfect for photos and a breath of fresh air -Small group setting for a more personal and immersive experience -Ideal for couples, friends, and wine lovers looking for a refined day out

$1,198.95

West Point and Bear Mountain Private Tour with Hotel Pick-up

Discover the beauty and history of the Hudson Valley on a private full-day tour to Bear Mountain State Park and the United States Military Academy at West Point. Travel in comfort with a professional guide and driver. Along the way, enjoy sweeping Hudson River views, explore the scenic landscapes of Bear Mountain, and take part in the official West Point visitor tour to learn about one of the most respected military academies in the United States. With convenient hotel pickup and drop-off in NYC, this experience offers a relaxed and memorable escape from the city. - Private Hudson Valley tour visiting Bear Mountain State Park and West Point Military Academy - Scenic drive through the Hudson Highlands with stunning Hudson River views - Opportunity to experience Bear Mountain hiking areas and seasonal fall foliage - Comfortable travel with a professional guide and driver in a Suburban or Escalade

$1,198.95

Private Trip to Woodbury Outlet with Hotel Pick Up

A trip to Woodbury Common Premium Outlets promises a delightful shopping spree, where you can explore an extensive selection of luxury brands at unbeatable prices. Begin your adventure with a comfortable pickup from your hotel lobby, and unwind in a private car as you journey to retail bliss. Spend time shopping at over 220 designer outlets, finding amazing deals on top brands. Afterward, take in the beauty of Hudson Valley with a scenic stop and the option to visit the Storm King Art Center. This stress-free, private experience is perfect for those looking to shop, explore, and enjoy a day out. - 220+ designer outlets with exclusive discounts - Scenic drive through the Hudson Valley - Option to visit Storm King Art Center - Private car transportation for a comfortable experience - Stress-free, luxury shopping experience

$1,198.95

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