Red Hook

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.

By car

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.

By train

You can take Amtrak to Rhinecliff and then take a taxi. Taxis are expensive, however, so get a ride from someone if you can.

By car

To get around this area, for the most part, you will need a car. Cycling and hiking are possible in decent weather.

By bus

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.

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

  phone: +1 845-758-6822
  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. There are student-guided tours arranged by the Admission Office, but you can also obtain a self-guided tour pamphlet and a map in that office, or at the kiosk in front of it. In addition, there are concerts and other events at Bard that are open to the public.

• Memorial Park (Town Green)

  address: Red Hook Village
  The park itself includes a dignified war memorial and a pretty little garden. There are also two beautiful houses right across the street from the park, one of which is an inn that is still in use. Worth a stop if you are driving up Route 9.

• Montgomery Place

  phone: +1 845-758-5461
  address: 25 Gardener Way, Annandale-on-Hudson
  380-acre historic site overlooking the Hudson, including a grand mansion. The grounds are lovely, with great views of the Hudson, and are home to lots of wildlife. The property also includes signposted trails, the best of which is the Sawkill Trail, which you can follow to see a view of a beautiful little waterfall which was depicted in art starting in the 1820s. This property was acquired by Bard College in 2016 and is officially called Montgomery Place Campus.

• Tivoli Bays

  phone: +1 845-889-4745
  This is an extensive estuarine wildlife preserve, consisting of marshes, mud flats and forest. Parts of it can be accessed by car or bicycle, other parts by canoe if you have one (there is a canoe launch in Tivoli North Bay), and there are numerous foot paths. Camping is not allowed in Tivoli Bays.

• Alison Wines & Vineyards

  address: 231 Pitcher Lane
  Tours and tastings from mid-April through December, Sa-Su 11AM-5PM. Views of the Catskill Mountains.

• Mead Orchards

  address: 15 Scism Rd, Tivoli
  Pick your own fruit and vegetables.

• Montgomery Place Orchards Farm Market

  address: 4330 Rt 9G, Red Hook
  Really worth stopping at this stand for fresh fruit, such as outstanding peaches in season. They also make good jams that are only slightly sweetened.

• Santa Fe52 Broadway, Tivoli. Exceptionally popular Mexican with emphasis on fresh produce and bold flavors.

• Traghaven

  phone: +1 845-757-3777
  address: 66 Broadway, Tivoli
  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.

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

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.

To the south, Rhinebeck is a small town, but much bigger than Red Hook, full of lovely houses, and a good place for a stroll in good weather.
To the north, Hudson has a long strip of great buildings on Warren St.
To the west, across the Kingston-Rhinecliff Bridge, are the city of Kingston and the Catskill Mountains.
To the east are the states of Connecticut and Massachusetts.