Choose the warmest, sunniest day possible to install the roofing during the winter months. Plan on a day when the temperatures will reach above 50 degrees Fahrenheit. Check the weather forecast to ensure you have several days of dry weather in store after the installation.
Roll out roofing felt at the eave first and attach the felt with a staple every 12 inches. Cover the roofing felt with shingles, leaving the edges of the shingles hanging off of the roof edges by about an inch and over the edge of the eave by 1-1/2 inch. Put four nails through the top of each shingle to secure it to the roof then install a second row of shingles over the top of the first row by the eave for double protection.
Install the rest of the shingles on the first side of the roofing in layers, putting down a strip of roofing felt and then a layer of shingles. Lay the roofing felt so that it overlaps the tops of the shingles in the row below it by about 8 inches and lay the shingles to overlap the row of shingles below by one-third to one-half the height of the shingles. Install the final row of shingles on the side so that the shingle tops sit even with the roof peak.
Layer roofing felt and shingles on the opposite side of the roof, starting with a double row at the eave and working upward in rows. Install the top row to line up with the roof peak.
Top the roof with wood ridge caps. Center the caps over the peak and secure the caps in place with four to six nails on each side of the cap.
Cover the exposed nail heads in the ridge caps with silicone caulk applied with a putty knife. Line all of the seams in the roof, between shingles and between rows, with a bead of silicone caulk to create a seal that will protect the new roofing throughout the winter.