An iconic house on an iconic road in an iconic town. Striebel Road is one of the most famous roads in this historic art and music filled town of Woodstock, New York. Striebel Road is a private road with only a handful of homes. The road was made famous by the one and only Bob Dylan. The artist, his manager, and many other musicians called this road home.
A short 10 minute walk from the house is the famous Bearsville theater, founded by Dylan’s manager. The theatre still hosts both young and emerging bands and established rockers. The Rolling Stones have used the Bearsville Theatre to rehearse before tours. The complex also houses restaurants, bars and an ice cream shop. Meanwhile, the town center of Woodstock is only a few minutes drive away. If you are feeling ambitious, it’s a 30 minute walk and I do it often. The town has experienced a massive resurgence of new restaurants and shops. See my shopping guide for my favorites below.
I recommend visiting the Sunflower Market in town for a larger grocery shopping experience. Not to be confused with Sunfrost Market which is just a moments drive from my home. I absolutely love Sunfrost and I go there often for breakfast, they have the best breakfast burritos. You can also find local produce. There is a CVS in town if you are in need of a local pharmacy. If you want to BBQ on the BREEO, Woodstock Meats is the place to go. You can find BBQ tools inside the lower drawers on the kitchen island.
In need of wine? Next door to Sunflower Market is a great wine store called Unfiltered. This is by far my favorite wine shop in town.
There are so many great restaurants within 10 minutes of my home. You will also receive a $20 gift card to Woodstock Brewing with each check-in. I am an owner of Woodstock Brewing and I recommend you go there! They have great beer, wine and burgers! My other favorites are below:
Cucina in Woodstock: @cucinawoodstock
A Woodstock Italian favorite. From homemade pastas to amazing thin-crust pizzas. Great for couples, groups and families. When I am in Woodstock I am a regular there and the penne puttanesca and rigatoni with sausage are my favorites.
Sylvia: @syvliawoodstockny
I know the owners well and I can’t suggest Sylvia enough. An open kitchen with a wood-fired grill and pantry of organic vegetables reflects their dedication to locally-sourced ingredients. Reservations are a must. Chef Doris Cho was nominated for a James Beard Award and is so well deserved.
Good Night: @goodnightwoodstock
The team at Sylvia recently opened this Asian fusion spot. It’s delicious if you are in the mood for unique Asian dishes. The bar is absolutely gorgeous! It's also a 4 minute drive from The Ranch. I suggest you take the back road, Glasco Turnpike to get there. This avoids any town traffic.
Garden Cafe: @gardencafewoodstock
This vegan juice and food bar serves delicious food, even if you are not vegan. They have a gorgeous garden which I recommend visiting for lunch if you are visiting upstate on a nice day to sit outside. They make great smoothies, juices and platters. I am a meat eater and I love their food. Their burritos are great and their brownie sundae is delicious.
Woodstock Brewing: @woodstockbrewing
You can pick up beer to drink at home or go for lunch. They make amazing burgers, tacos and the onion rings are off the charts.
Maria Vera Skincare : @mariavera_skincare
Located in Kingston, Maria and her team are the best facialists in the Hudson valley. I often get a series of microcurrent sessions when I am upstate. You will literally leave feeling 5 years younger. I have been visiting Maria for well over a decade. I adore her. You can read about my treatments here. You do need to book well in advance of your trip The Ranch. Maria's studio is about a 15 minute drive from The Ranch.
Three Turtle Doves Vintage Finds : @threeturtledoves
Want some amazing vintage finds? Heather’s shop is divine. You cannot miss it. She also carries gorgeous jewelry and some of the best picks from Helena Christensen’s staerkandchristensen clothing line. Every time I am back home I make a trip in and come away with a gorgeous new piece of jewelry or vintage bag. Heather's shop is right in town, less than a 5 minute drive from The Ranch so you really have no excuse not to go.
The Red Foxxx : @shoptheredfox
This sweet lingerie store opened last year and I adore it. Classic, simple, chic lingerie and loungewear. It’s located a few stores down from Three Turtle Doves. I have found some of the cutest things there. Must go!
Shakti Yoga : @shaktiyogawoodstock
Founder Linda Winnick is a dear friend of mine and she now has locations in Woodstock and Saugerties. Drop in for a class or reach out for a private session with one of her teachers. Contact Linda at 845.389.5826. If you contact Linda, tell her Robin sent you!
Overlook Mountain: You can find this challenging trail a short drive from The Ranch. The view is simply fantastic but be prepared to walk 2.5 miles up a steep and rocky trail. This is one of my favorites for really burning some calories! The hike does get crowded so I suggest arriving by 9am to secure parking. The police do give parking tickets if you park at the nearby monastery rather than the main parking lot.
Kaaterskill Falls Hike: About a 30 minute drive from The Ranch but a must if you are eager to see a waterfall. It is one of the most popular hikes in the Catskills because it is New York’s tallest waterfall! The round-trip trek is 1.4 miles.
Hunter Mountain Skiing: A premier ski destination in the Catskills. Hunter features a 1,600-foot vertical drop. Hunter was the first ski destination in the state of New York to install snow-making, the first in the world with top-to-bottom snow-making, and the first in the world to have 100-percent snow-making coverage of the mountain. The resort offers snow tubing as well as skiing. Hunter Mountain also features four terrain parks and holds freestyle events throughout the ski season.
Ashokan Rail Trail: The Ashokan Rail Trail is an 11.5 mile recreational haven that welcomes hikers, bikers, snow show shoers and skiers! The whole stretch can be finished in 3 to 3.5 hours. The trail is flat and easy and can be enjoyed all year. While the trail is unpaved, the surface is a smooth crushed stone that is suitable for most bikes. The trail is also very wide, ranging from 10 to 12 feet in width, which is a lot wider than most bike paths in our region. The result is a beautiful trail experience that feels uncrowded. This about a 15 minute drive from The Ranch.
Windham Skiing: Windham Mountain is mostly a beginner-friendly ski area, with about 20% of its trails as easy. Windham Mountain is the closest big mountain skiing to the city. It has 54 trails and 12 lifts, including four high-speed detachable lifts. One being a express 6 Pack and three high speed detachable quads. The resort stretches across two mountains, The highest peak is situated at 3,100 feet (940 m) with a vertical rise of 1,600 feet (490 m) from the base. Snowmaking covers 98% of the trail area of 285 acres (1.2 km2). The resort has 6 terrain parks that are great for all skill levels of park skiing.