Red Hook, NY Road Trips

This is a very pretty area of the Hudson Valley, characterized by countryside and small towns. Stores commonly close early, and in places like the tiny village of Tivoli, most stores and restaurants never open at all on Tuesdays. The Village of Red Hook, though small, is the largest population center in the Township of Red Hook, and has a center that's more than the single (albeit nice) street and crossroads of Tivoli. Annandale-on-Hudson, on the other hand, has no center other than perhaps Bard Central Campus, which doesn't really function as a downtown, as the land is privately owned and it lacks the shops and restaurants of a typical downtown. The Red Hook Area Chamber of Commerce provides tourist information.

In addition to the following attractions, the villages of Red Hook and Tivoli contain some beautiful antique buildings, many of them private houses. Some are truly unique in shape. If you want to see them, you are best off walking the few streets of Red Hook's small downtown and on Montgomery St for some ways to the south of Broadway in Tivoli. Broadway almost singlehandedly constitutes the downtown area of Tivoli, approximately from just east of Montgomery St to St. Sylvia's Catholic Church. That stretch is quaint and well worth a walk, which is unlikely to take an able-bodied person more than 10 minutes even if done in a leisurely fashion. Bard College (Campus Road, Annandale-on-Hudson), ☏ +1 845-758-6822, toll-free: +1-800-BAR-DCOL (227-3265), [email protected]. Office of Admission is open M-F 9AM-5PM during the academic year. Bard College has a lovely campus that is well worth visiting if you are driving in the area. The architecture varies from Victorian and neo-Gothic style to Frank Gehry. There is also Blithewood Garden — a beautiful garden with big rose bushes, statuary, and a great view across the Hudson, downhill from a Victorian mansion that now houses the Levy Economics Institute — and a separate pleasant modern take on a Japanese rock garden island with a distinctive footbridge to get there and a moat full of carp, with the pretentious name of "Parliament of Reality," across campus near the Gehry-designed Fisher Center. Much wildlife lives on campus, including hares and several varieties of pretty butterflies.

Mead Orchards, 15 Scism Rd, Tivoli, ☏ +1 845 756-5641. August through October only, 10AM-5:30PM, weekends and Monday holidays. Pick your own fruit and vegetables.

Flatiron Restaurant, 7488 South Broadway, Red Hook, ☏ +1 845-758-8260. Tu – Sa: 5pm – 9pm; Su - M: closed. Tasty American restaurant with some imaginative touches. Half the entrees are steak, but not all the sauces for the steak are typical of steakhouses: for example, there is an habanero sauce. Mid-priced and a good value, as, for example, you can get a hanger steak frites with 6 oz of meat for $28. They also have a great pastry chef, so try to leave room for some dessert. Appetizers: $12-24; burgers: $16-24; entrees: $24-52; sides: $6-9. (updated Aug 2025) Santa Fe, ☏ +1 845 757-4100. 52 Broadway, Tivoli. Exceptionally popular Mexican with emphasis on fresh produce and bold flavors.

Traghaven, 66 Broadway, Tivoli, ☏ +1 845-757-3777. Open daily at 5PM, closed Mondays. This is a whiskey bar with a great selection, including local whiskeys like Taconic. You can have whiskey flights if you'd like to taste 3 whiskeys; they charge you the shot price for each whiskey, which is about 1/2 the menu price (so a whiskey costing $15 on the menu would cost you $8 as part of a flight). This is also a true restaurant, with food of much higher quality than bar food. For example, their salads use fresh ingredients (their house salad uses a lot of poppy seeds and one of their dressings is a very well-made carrot vinaigrette), not fumigated tomatoes, and their steak frites are excellent on both counts. Their food portions are humongous, so unless you have a tremendous appetite, you may be best off sharing things. Desserts are also high-quality; for example, they make delicious fudge in-house for their ice cream sundaes. (updated Aug 2016)

There are several inns in the Village of Red Hook and a couple of hotels in Tivoli.

Car is your best bet. The main north/south road in the area is Route 9, which bisects the village of Red Hook and connects it with Rhinebeck, to its immediate south. Its local offshoot is Route 9G, which is one lane each way, and enables you to get to Bard College and Tivoli. You can take Amtrak to Rhinecliff and then take a taxi. Taxis are expensive, however, so get a ride from someone if you can. You might get somewhat better prices by using Uber, but Lyft will likely cost more.

To get around this area, for the most part, you will need a car. Cycling and hiking are possible in decent weather. Dutchess County does have a bus service , but it runs infrequently and its schedule is not regularly updated either in print or on their website. So you may find that you are waiting in a place no longer designated as a bus stop, and watch the last bus of the night whiz by you. If you choose to use the Dutchess County Loop Bus, consider calling their phone number, ☏ +1 845-473-8424, to double check on current times and bus stops.

If you are driving, watch out for deer on the road and cyclists or pedestrians on the side of the road. Deer cross very often, sometimes darting headlong into traffic without warning, and you really don't want one to go through your windshield if you can avoid it. If you are cycling or walking on the side of 9G, be very mindful of motor vehicle traffic. This narrow road is a major thoroughfare in the area, it lacks any sidewalk, and many motorists speed. There have been some fatal accidents involving pedestrians. If you are hiking, watch out for deer ticks that can spread lyme disease, as they are prevalent in the area. Poison ivy is also present in wild country like Tivoli Bays. And mosquitoes, though usually not spreading disease in the area, are a pain, as are chiggers, which can bite your feet without your even noticing them until the next day. Consider using an insect repellent.