The oldest building in Montauk  is the Second House Museum (Second House Rd., off Montauk Hwy./Rte. 27, west of the village, 631/668-5340, 10 a.m.–4 p.m. Thurs.–Tues. July–Oct., 10 a.m.–4 p.m. Sat.–Sun. June, adults $2, children $1), a dark and long-ceilinged affair, first built in 1746 and rebuilt in 1797. Inside you’ll find period furniture and small, casual exhibits on Montauk history.
One of the most interesting displays concerns Samson Occom, a Monhegan Indian born in Connecticut. Occom came to Montauk in 1744 after converting to Christianity. He married a Montauk woman and became a noted preacher, as well as the author of several hymns still sung today.
Together with two white ministers, Occum went to England in the 1760s to raise money for indigent Indians. The earl of Dartmouth was so impressed with Occum’s powerful preaching that he donated £10,000 to the cause.
Back in America, however, the white ministers took over administration of the funds—which they used to found Dartmouth College  in 1769. Occum withdrew from village life, a disillusioned, discouraged man.
The Third House, in Theodore Roosevelt County Park (off Rte. 27 east of the village center, 631/852-7878, 10 a.m.–5 p.m. Wed.–Sun. June–Sept., free admission) is a big, rambling affair several times the size of the Second House. Set in the middle of what is now Theodore Roosevelt County Park, it was used by Teddy Roosevelt and his Rough Riders in 1898, and currently functions as the park headquarters. In the house is a small exhibit on Roosevelt and his troops, along with early Montauk artifacts.