1953 - 1959
* Annawan Centennial celebration is held on September 4th and 5th *
* Kiwanis Club is formed - charter being received on December 7th *
* William Odgen's harness and general store is closed after 50 years of operation *
* New Annawan High School opens on Tuesday, August 28th *
* Fairview United Evangelical United Brethren Church builds new parsonage - dedicated October 14th *

1960- 1969
* Allied Veterinary Service operated by Dr. Harker and Dr. Swinderman opens *
* A new building housing Turn Coin Wash and Johnson Electric opens *
* Lowell Mapes secures the winning bid for constructing a new building on the east end of the village *
* Sacred Heart Church breaks ground for their new rectory *
* Mineral High School students attend Annawan on a tuition basis *
* Work progresses on Interstate 80 north *
* Mineral School District annexes to the Annawan district *
* Seven mile stretch of I-80 between Atkinson and Annawan opens *
* Village Council annexes 40-acre tract north of the village to I-80 *
* Annawan-Alba Library moves into Annawan Township Hall *
* Final link of I-80 opens - Governor Kelly is present for the opening *
 * Farmers Grain Elevator opens new facility *
* Mr. and Mrs. Clarence Robinson purchase Wayne Feed Outlet *
* Annawan Booster Club is formed with Vernon Williams as president *
* Ben Franklin Variety Store opens *
* Open house is held for the new fire station *
* Annawan Shell Station is under construction *
* Announcement that the Annawan Railroad Depot will be closed *
* Tri-County Municipal League is formed involving 16 area communities *
* Fred E. Johnson, Rock Island Railroad employee, retires after serving as depot agent in Annawan, 1939 to 1966 *
* Clarence Davidson, Davenport, takes possession of restaurant (The Edgeatowner) at Tom Lanes*
* Dedication of new veteran's memorial monument in Village Park *
* Village of Annawan and Kiwanis Club purchases new street lights *
* A ten acre tract in Ferguson Addition on the south edge of the village owned by Albert Pritchard and Perry Munson is surveyed for a new housing addition *
* Village purchases property from Chicago, Rock Island, and Pacific Railroad as Mayor Henry Nowers receives information that the railroad is selling "all excess property" along the railroad lines *
* William Dynes Sr. and William Dynes Jr. families host approximately 230,000 visitors to a three day farm equipment show sponsored by M&W Equipment *
* Faye Gish and Gail Christian, area businessman, announce plans to open a Dairy Sweet drive-up ice cream business *
* Sauk Trail Inn Restaurant is built by Ufheil family opens for business *
* Annawan High School completes first Building Trades house under the direction of Dennis Heavener - the class built five houses in the village under a ten year period *
* A group of 30 area businessmen and farmers form a corporation (Annawan Bank Company) and purchase the controlling stock in the State Bank of Annawan and the entire assets of the Johnson Insurance Agency *
* Mr. and Mrs. Earl Salzmann will manage the new Texaco Station located on Route 78 *
 

1970 - 1979
* State of Illinois takes over control of the Hennepin Canal *
* Sauk Trail Inn expands facility *
* New Annawan street (Doye Street) is named in memory of AHS graduate, Rick Doye, who was killed in Vietnam *
* Work begins on Farmer's Table restaurant to be built at an approximate cost of $100,000 *
* Village Board accepts bid from the State Bank of Annawan for a lot on Front Street *
* Annawan Motor Sales expands by adding on to the west side of their current building
Tomahawk, an economy gas station, is to be built on Route 78 near I-80 by Tom Ingram *
Annawan-Alba Fire Department purchases first rescue van *
* Farmers Building Service, owned by Charles Farmer Jr starts metal building business *
* Ribbon cutting ceremony conducted for new building housing the State Bank of Annawan*
* Open house held at newly remodeled Goossen's Plumbing and Air-Conditioning - the store will also include a floor covering and interior decorating section *
* Charles Farmer Sr. purchases part of the Verdick Implement dealership *
* Bill Rambo takes over Bill's Shell from Bill Comp *
* The new Annawan Grade School opens on August 27th *
* Verdick Implement owned by Charles Farmer Sr. builds a new facility, south edge of the village*
* Annawan Village is awarded $11,500 EPA grant earmarked for wastewater treatment works study *
* Annawan Jaycee chapter is organized *
* Village Board approves eight lot subdivision on old grade school property *
* New rolle bolle courts constructed by Bolders club behind the current fire station *
* William Baker present Annawan Kiwanis Club with $10,000 check to add an open air picnic shelter *
* Annawan-Alba Library hosts an open house to introduce the "new" historical jail annex of the library *
* Annawan celebrates its 125th birthday on June 4th *
* Arden and Regina Williams open Angela's Apparel Store *
* Village Board agrees to purchase a 12 acre plot for the community park *
* Three new businesses open in the lower level of the Annawan Bank *
* Ferguson Auto Repair expands business by purchasing a building owned by Chet Goossens *
* John Hatzer and Mike Nordstrom purchase implement company from Charles Farmer and Associates *
 

1980 - 1989
* Jaycees finalize plan to start youth football program *
* Annawan wins bid to host World Rolle Bolle tournament *
* Chet and Gretchen Goossens before proprietors of an ice cream and sandwich shop *
* Annawan Jaycees continue to grow with 80 members *
* Construction begins on the new sewer system *
* A new 1500 square foot dental office is built by Dr. Tom VanVooren *
* Carol Croegaert opens The Cactus Patch floral shop *
* Wayne Heitzler and James Wiley purchase Tom Lanes Bowling *
* Terry and Vicki Dickens are the new owners of The Longhorn *
* Brave Industries takes possession of former John Deere Implement of the east edge of town *
* New 250,000 gallon water tower built *
* Co-op Gas and Oil constructs a new plant east of Annawan *
* Brave Industries plans a 3,000 square foot expansion to its 10,000 square foot facility *
* Village takes over ownership of VFW/American Legion building *
* New Annawan firm, American Eagle Buildings, opens *
* Fort Annawan, formerly Sauk Trail Inn, re-opens with $40,000 sign to attract I-80 business*
* Village Board and Jim Howell each donate $2,500 to begin construction of a shelter and pay off baseball fence loan at Howe's Park *
* Annawan, Atkinson and Geneseo form joint Vocational Coop *
* Harry Heath's Barn Burner Recording Studio nears completion *
* Lynn Williams opens a carwash on Second Street *
* Jane Savage opens a new shop, Annawan Village Interiors *
* Annawan water treatment plant named one of the best six in Illinois - Jay Bridges is the water superintendent *
* Annawan High School's ACT test scores are ranked 2nd in the State of Illinois *
* Johnston Lumber Company replaces their 88 year old storage building with a new 64' by 120' structure *
* Stackhouse-Moore renovates funeral home *
* 1990-Robert G. Lenertz assumes duties as president of The State Bank of Annawan *
* Bob and Isle Davis purchase Purple Onion restaurant *
* Michels Pipeline Construction Company begins laying a fiber-optic cable from Green River to Annawan for Henry County Telephone *
* Fort Annawan reopens - an east coast firm is leasing the property from I-80 Truck Stop *
* Annawan Brewing Company, formerly the Old Timer, reopens *
* Jim and Terri Wiley become sole owners of Tom Lanes bowling alley *

1990 - 1999
* The AHS agriculture department and the community work together to build a new locker room near the football field *
* The New Kids on the Block have recording session at The Barn Burner Recording Studio *
* Duane and Mindy Bollengier purchase Tom Lanes *
* Allen Nordquist, Larry Carlson, and Nancy Kelly become new owners of the Johnston Lumber Company *
* Village Board purchases the Farmer's Table for $13,500 *
* Randy Hanson opens Hanson's Landscaping *
* Norton Insurance Agency moves into newly remodeled offices *
* Wayne Heitzler and Terry Dickens purchase the Annawan Farmer's Table from the village*
* Don Moon sells his insurance agency after 37 years of business *
* Cliff Verdick retires as Annawan Fire Chief after 37 years *
* Janet Wancket purchases the Purple Onion Restaurant *
* Mary Sue Moon opens Memory Lane Quilt Shop *
* Kathy Rakestraw and Maureen Hasbrook open flower shop *
* Colin and Liz DeVrieze purchase bowling alley *
* Car wash and repair shop owned by Craig and Doreen Miller opens for business *
* The Regional Office of Education opens in newly renovated office *
* Williams IGA opens for business as the Annawan Hometown Market - owned by Lynn Williams and Jeff Roman *
* Wilbur Hodgett, Annawan mayor, dies *
* Jeff and Charles Farmer, Leading Edge Development, open subdivision on the south edge of the Village *
* Dennis DeSplinter, becomes mayor of Annawan *
* Welcome to Annawan signs are constructed and installed by the Annawan FFA *
* Mary and Mike Wheeler open Antique Alley *
* Village opens new offices in the ROE complex  owned by the village *
* Pawel and Eva Przbyla open the Annawan Bread Box bakery *
* Larry and Jeanne Carlson become sole owners of the Annawan Building Center *
* Annawan Community Economic Development Corporation (ACEDC) is formed *
* Bill Rambo and Maurice Atwell retire from the Annawan Fire Department *
* The Annawan School Board purchases 3 acres west of the school for P.E. and football practices*
* Annawan hosts National Quilt Show organized by Mary Moon *
* Edna Jo's Hair Care Service begins business * 
* Shaun Kiene purchases the Loft Restaurant *
* Annawan Home Center is purchased by Mike Hill *
* Dr. Jeffrey Lathrop opens new chiropractic clinic *
* Loren and Val Jackson open Jackson's Collision Repair
* The Village of Annawan sells the building housing the ROE *

2000 - Present
* Chuck and Davette Malufka open a video and music store *
* Annawan Village offices move to new location in the former Hanson Landscaping building *
* Sugar Shack, ice cream parlor, opens for business *
* Representative Don Moffitt and Senator Carl Hawkinson present the Village with a check for $32,500 for the purchase of two severe weather-warning sirens for the Village *
* ACEDC initiates a "Welcome Package" for new residents *
* Kennard Franks becomes mayor of Annawan *
* Deb Pool purchases the former Memory Lane building *
* Annawan Kiwanis Club constructs and erects a new church signage board and planter near the community center *
* Village uses a $71,000 Illinois First Grant to demolish grain elevators * 
* Olympic Flame Restaurant opens *
* Holiday Inn Express is opened *
* JTJ Enterprises purchase the Annawan Car Wash on Route 78 *
* Beck Oil Company of Princeton purchases the Phillips 66 Shop and Go *
* Speaker of the U.S. House of Representatives, Dennis Hastert, visits Annawan*
* Emma's Bloomers moves two stores east *
* New gas station, Mobil Bulk Petroleum, is built *
* Annawan Banquet and Convention Center opens adjacent to the Holiday Inn Express *
* Troy and Michelle Osborne open The Styling Station Salon *
* Improvements to Route 6 start, not expected to be done until 2005 *
* The Pizza Box opens *
* Village annexes approximately 400 acres, doubles size of Annawan *
* TIF district developed in home of future industrial site *
*Longhorn sold and reopens as The Phoenix*
*Congressman Dennis Hastert gifts the village $1.84 million for road construction to Industrial Park*
*New streetlights placed in downtown Annawan, Village Board member Grove Killelea spearheads the successful program*
*Road construction complete, sod to be laid in 2006*
*Ethanol plant determined to be placed in Annawan, construction to begin in 2006*
*Patriot Renewable Fuels opens office in Annawan*
*Second TIF developed in Annawan*
*Holiday Inn is changed to Annawan Express*
*Annexed additional property into town, village now goes into Bureau County (2007)*
*Major improvements are being done to US Route 6 in preparation for ethanol plant traffic (2007)*
*People's National Bank of Kewanee opens branch on Route 78 (2007)*
*Patriot Renewable Fuels moves offices to plant site (2007)*
*State Bank of Annawan becomes BankORION (2007)*
*Bourbon's Place opens in the former Phoenix building (2007)*
*Annawan Express sold, will open as a Best Western (2007)*
*Grove Killelea, Village Board trustee, passes away (2007)*
*Annawan's oldest living citizen - Lois Dynes - passes away on January 21, just 21 days before her 109th birthday (2008)*
*Dean's Tap is sold and reopens as JA's (2008)*